Downstream synthetic route of 777-12-8

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

777-12-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.777-12-8,6-(Trifluoromethyl)benzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

To a solution of 6-(trifluoromethyl)-2-aminobenzothiazole (218 mg, 1.0 mmol) in dichloromethane (20 mL) was added l-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1 -hydroxy- 1 ,2, 3 -benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{5-[l-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-lH-5-pyrazolyl]-2- methoxyphenoxy}aceticacid (3) (458 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25 ¡ãC for 24h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (lOi) (528 mg, 80percent yield). NMR (CDC13): 8 10,82 (br s, 1H), 8.11 (s, 1H), 7.88 (d, 1H, J = 7.9 Hz), 7.67-7.70 (m, 1H), 6.98-7.02 (dd, lH, J = 7.9, 1.6 Hz), 6.96 (s, 2H), 6.90-6.94 (m, 2H), 5.51-5.56 (dd, l H, J = 1 1.9, 3.9 Hz), 4.79 (s, 2H), 3.99 (s, 3H), 3.91 (s, 6H), 3.89 (s, 3H), 3.71-3.79 (dd, lH, J = 11.9, 17.5 Hz), 3.10-3.15 (dd, 1H, J= 17.5, 4.7 Hz), 2.43 (s, 3H); ESIMS:659 (M+l)+.

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; AHMED, Kamal; REDDY, Adla, Malla; PAIDAKULA, Suresh; RAO, Neigapula, Sankara; SHETTI, Rajesh, V., C., R., N., C.; WO2012/104857; (2012); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 777-12-8

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.777-12-8,6-(Trifluoromethyl)benzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

Example 2: General procedure for synthesis of compounds 24 and 46. (0108) (0109) General methodology: In a microwave vial benzothiazole derivative and the corresponding isocyanate is added in each case. Next, THF is added as solvent. The vial is introduced into the microwave reactor and heated to the temperature for the time indicated in each case. After the reaction time, ethyl acetate (50 mL) and water (50 mL) is added. The organic phase is dried over anhydrous MgS04 and the solvent is removed under reduced pressure. The obtained residue was purified by flash column chromatography using Isolera One equipment, in all cases a mixture of hexane and ethyl acetate as eluent was used. N-(6-trifluoromethylbenzothiazole-2-yl)-N’-(3-chlorophenyl)urea (24): (0110) Reagents: 1-isocianato-3-chlorobenzene (175.8 mg, 1.2 mmol), 2-amino-6-trifluoromethylbenzothiazole (250 mg, 1.2 mmol) and THF (0.4 mL). Reaction conditions: 3 hours and 30 min under microwave irradiation at 110¡ãC. Purification by flash column chromatography using hexane/ethyl acetate (3:1) to obtain a white solid. Yield: 43.2 mg, 10percent. Mp: 222¡ãC-223¡ãC 1H NMR (500 MHz, DMSO-d6) delta: 11.16 (s, 1 H), 9.38 (s, 1 H), 8.41 (s, 1 H), 7.73 (s, 1 H), 7.69 (dd, J = 8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.35 (t, J = 7.9 Hz, 2H), 7.11 (d, J = 8.5 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) delta: 162.6, 152.0, 140.3, 133.7, 131.0, 125.0 (q, J = 271.7 Hz), 123.6 (d, J = 31.8 Hz), 123.5, 123.4 (d, J = 2.5 Hz), 120.1 (d, J = 4.3 Hz), 118.8, 117.9. HPLC purity: >99percent. MS (ES) m/z: 372 [M+H]+., 777-12-8

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; Consejo Superior De Investigaciones Cientificas (CSIC); MARTINEZ GIL, Ana; PEREZ FERNANDEZ, Daniel Ignacio; GIL AYUSO-GONTAN, Carmen; GARCIA SALADO, Irene; REDONDO SANCHO, Miriam; PEREZ MARTINEZ, Concepcion; EP2949651; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 777-12-8

As the paragraph descriping shows that 777-12-8 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.777-12-8,6-(Trifluoromethyl)benzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

777-12-8, 102031 5 -chloro-2-methoxy-3 -ethylbenzoic acid (100mg, 0 .467mmo1) was dissolved in DMF (5m1). HBTU (2 13mg, 0.56 immol) was added followed by DIPEA (244u1, 1.4Ommol). The resulting mixture was stirred at rt for l5mins, then 6- (trifluoromethyl)benzo[d]thiazol-2-amine (102mg, 0 .467mmo1) was added. The resulting mixture was stirred at 120¡ãC for 24h. Saturated NH4C1 solution was added and extracted with EA for two times. The combined EA layer was dried over Na2504 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography to give title compound as a yellow powder (115mg, 62percent). ?H NIVIR (300 IVIFIz, Acetone-d6) 8.40 (s, 1H), 8.10 (s, 1H), 7.90 (d, J = 8.7 Hz, 1H), 7.81 (d, J = 8.1 Hz, 1H), 7.39 (s, 1H), 2.72 (q, J=9.OHz, 2H), 1.24 (t, J = 9.0 Hz, 3H). MS (ESI) [M+H]requires m/z 401.03, found m/z400.6.

As the paragraph descriping shows that 777-12-8 is playing an increasingly important role.

Reference£º
Patent; JIN, Shengkan; AUGERI, David J.; CAO, Bin; TAO, Hanlin; (126 pag.)WO2017/201313; (2017); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Some tips on 777-12-8

The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

777-12-8, 6-(Trifluoromethyl)benzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

777-12-8, To a stirred solution of methyl 5-chloro-3-cyano-2-methoxybenzoate (86mg, 0.382mmo1) in MeOH (3m1) was added 2.0 ml iN KOH solution. The resulting mixture was stirred at 60¡ãC overnight. The solvent was evaporated out and 4N HC1 in dioxane (lml) was added to the residue. The mixture was stirred for another 10mm before it was concentrated and dried under vacumn. To this residue was added HBTU (172mg, 0.456mmo1), DMF (3m1) and DIPEA (330u1, 1.9 mmol). The mixture was stirred for lOmins and then 6-(trifluoromethyl)benzo[d]thiazol-2-amine (83mg, 0.3 8mmol) was added. The resulting reaction was heated at 120 ¡ãC for 24hs. After cooled to rt, the mixture was separated between EA and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography gave the 5-chloro-3-cyano-2- hydroxy-N-(6-(trifluoromethyl)benzo[d]thiazol-2-yl)b enzamide as a yellow solid (62mg, 42percent). ?H NMR (300 IVIHz, Acetone-d6) 8.31 (dt, J = 1.6, 0.9 Hz, 1H), 7.85 (d, J = 3.0 Hz, 1H), 7.79 -7.65 (m, 2H), 7.14 (d, J = 3.0 Hz, 1H). MS (ESI) [M+H] requires m/z 398.00, found m/z 397.95.

The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JIN, Shengkan; AUGERI, David J.; CAO, Bin; TAO, Hanlin; (126 pag.)WO2017/201313; (2017); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 777-12-8

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.777-12-8,6-(Trifluoromethyl)benzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

777-12-8, To a stirred solution of methyl 5-chloro-2-methoxy-3-((methoxymethoxy)methyl)benzoate (122mg, 0.445mmo1) in MeOH (5m1) was added 2.2 ml iN KOH solution. The resulting mixture was stirred at 60¡ãC overnight. After cooled to rt, the reaction was partitioned between EA and 2percent citric acid. The EA layer was washed with brine, dried over Na2504 and concentrated in vacuo. To this residue was added HBTU (98mg, 0.258mmo1), DMF (3m) and DIPEA (187u, 1.075 mmo). The mixture was stirred for lOmins and then 6-(trifluoromethy)benzo[d]thiazo-2-amine (47mg, 0.2l5mmo) was added. The resuting reaction was heated at 120 ¡ãC for 24hs. After cooed to rt, the mixture was separated between EA and water. The organic ayer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by coumn chromatography gave the 5- choro-2-hydroxy-3 -((methoxymethoxy)methy)-N-(6-(trifluoromethy)benzo[d]thiazo -2y)benzamide as a yeow soid (37mg, 39percent). ?H NMR (400 MHz, Choroform-d) 8.16 (s, 1H), 7.99 (d, J = 2.5 Hz, 1H), 7.91 (d, J = 6.1 Hz, 1H), 7.72 (d, J = 6.1 Hz, 1H), 7.48 (d, J =2.5 Hz, 1H), 4.80 (s, 2H), 4.78 (s, 2H), 3.47 (s, 3H). MS (ESI) [M+Na] requires m/z 469.02, found m/z 468.55.

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; JIN, Shengkan; AUGERI, David J.; CAO, Bin; TAO, Hanlin; (126 pag.)WO2017/201313; (2017); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Some tips on 777-12-8

The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

777-12-8, 6-(Trifluoromethyl)benzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of methyl 5-chloro-3-(2-(dimethylamino)ethyl)-2- methoxybenzoate (88mg, 0.324mmol) in methanol (5ml) was added IN potassium hydroxide (91mg, 1.62mmol, 1.62ml) solution. The mixture was heated at 60¡ãC overnight. IN HC1 was added to adjust the PH to 1. The mixture was concentrated in vacuo. The residue was dissolved in dimethylformamide (3ml). N,N,N’,N’-Tetramethyl-0-(lH-benzotriazol-l- yl)uronium hexafluorophosphate (71mg, 0.324mmol) was added followed by N,N- diisopropylethylamine (282ul, 1.62mmol). The resulting mixture was stirred at room temperature for 15mins, then 6-(trifluoromethyl)benzo[d]thiazol-2-amine (71mg, 0.324mmol) was added. The resulting mixture was stirred at 100¡ãC overnight. Saturated ammonium chloride solution was added and extracted with ethyl acetate for two times. The combined ethyl acetate layer was dried over Na2S04 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography to give title compound as a yellow powder (34mg, 23percent). 1H NMR (300 MHz, Chloroform-i ) delta 8.16 (s, 1H), 8.05 (d, J = 2.7 Hz, 1H), 7.91 (d, J = 8.6 Hz, 1H), 7.71 (dd, J = 8.5, 2.0 Hz, 1H), 7.50 (d, J = 2.7 Hz, 1H), 3.97 (s, 3H), 2.99 – 2.93 (m, 2H), 2.75 – 2.66 (m, 2H), 2.43 (s, 6H). MS (ESI) [M+H]+requires m/z 458.08, found m/z 458.15., 777-12-8

The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JIN, Shengkan; AUGERI, David J.; CAO, Bin; TAO, Hanlin; (126 pag.)WO2017/201313; (2017); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Some tips on 777-12-8

777-12-8, The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

777-12-8, 6-(Trifluoromethyl)benzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-(Trifluoromethyl)benzo[d]thiazol-2-amine (6.8 g, 31.16 mmol)was dissolved in THF (60 mL) under N2. Isoamyl nitrite (8.03 g,68.55 mmol) was added dropwise and the mixture was refluxed for1.5 h. Then the mixture was poured into ice-H2O (60 mL) andextracted with EtOAc. The organic layer was washed by saturatedaqueous NaCl and dried over Na2SO4. It was then concentrated andpurified via flash chromatography on silica gel to get 6 g (Yield43.2%) of 6-(trifluoromethyl)benzo[d]thiazole (21n) as a yellow oil.ES-LCMS m/z: 204.0 (MH).

777-12-8, The synthetic route of 777-12-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cao, Hengyi; Zhu, Guangya; Sun, Lin; Chen, Ge; Ma, Xinxin; Luo, Xiao; Zhu, Jidong; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Analyzing the synthesis route of 777-12-8

As the paragraph descriping shows that 777-12-8 is playing an increasingly important role.

777-12-8, 6-(Trifluoromethyl)benzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

777-12-8, 8.25 ml tert-butyl nitrite were added to a solution of 7.40 g copper (II) chloride in 120 ml acetonitrile. The reaction mixture was stirred ten minutes at room temperature. Then a solution of 10.0 g 2-Amino-6-(trifluoromethyl)benzonitrile were added. Then 100 ml 1 N HCI were added to the cooled reaction mixture. The reaction mixture was extracted five times with portions of 50 ml ethyl acetate. The combined organic layers were washed with water and the dried over MgSO4. The solvent was removed in vacuo to obtain 9.79 g crude 2-Chloro-6-trifluoromethyl-benzothiazole as a red oil which solidifies upon standing. This material was used without further purification. C8H3CIF3NS (237.63), MS(GC): 237.0 (M+H+), Rf(n-heptane :ethyl acetate = 1 :1) = 0.72 .

As the paragraph descriping shows that 777-12-8 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; WO2007/39176; (2007); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica