With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64987-16-2,Methyl 2-(2-aminothiazol-4-yl)acetate,as a common compound, the synthetic route is as follows.
64987-16-2, Each of Compounds 36 and 37 was synthesized as follows. Reaction of an amino substituted heteroaryl with (trimethylsilyl) diazomethane (2.0 M solution in hexanes) in a solvent of methanol and benzene yielded an intermediate. Substitution of the intermediate at C-4 position of DBD gave the desired product. See Scheme 2 below. Analytical data on Compound 36 are shown below. Compound 36, i. e., [4′-O-DEMETHYL-4 – [4″- (METHYL-O-ACETYL)-2″-] thiazolylamino] -4-desoxypodophyllotoxin. Yield 59%; Amorphous, mp [116-120 C] (dec. ); ESI MS: 553 [M-H], 577 [[M+NA]. LH] NMR [(CDC13)] [6] 6.85 (s, 1H, 5-H), 6.52 (s, 1H, 8-H), 6.38 (s, 1H, 5″-H), 6.30 (s, 2H, 2′, 6′-H), 5.98 and 5.96 (dd, 2H,- [OCH70-),] 5.16 (br, 1H, 4-H), 4. 59 (br, [1H,] 1-H), 4.40 (t, [1H, 11-H),] 3.95 (t, [1H,] 11- H), 3.79 (s, 6H, 3′, 5′-OCH3), 3.73 (s, 3H,-COOCH3), 3.60 (s, [2H,-CHACOOCH3),] 3.00 (m, 2H, 2-H, 2-H). Compounds 6,11, 38-42,77-82, 84,96, 118,126, 128,130-131, 140,145- 146,163, and 165 were synthesized by coupling an appropriate alcohol or amine to an amino substituted heteroaryl followed by conjugation with DBD. Analytical data on a number of compounds are shown below. Compound 39, i. e., [4′-O-DEMETHYL-40- [5″- (ETHOXYCARBONYL)-2″-] pyridylamino)]-4-desoxypodophyllotoxin. Yield 35 %; Amorphous, mp [164-168 C] (dec. ); ESI MS: 547 [M-H], 571 [[M+NA]. LH] NMR [(CDC13)] [S] 8.78 (d, 1H, [J] = 2.2 Hz, 6″-H), 8.04 and 8.01 (dd, J = 2.2 Hz, 1H, 4″-H), 6.79 (s, 1H, 5-H), 6.55 (s, 1H, 8- H), 6.42 (d, [J =] 8.8 Hz, [1H,] 5″-H), 6.33 (s, 2H, 2′, 6′-H), 5.99, 5.96 (dd, J = 1. 6 Hz, [2H,-OCHEO-),] 5.46 (br, 2H, 4-H, [NH),] 4.88 (d, J = 5.5 Hz, 1H, 1-H), 4.62 (br, 1H, [11-H),] 4.40 (br, [1H, 11-H),] 4. [36] (q, J = 7.1 Hz, 2H, [CH2CH3),] 3.79 (s, 6H, 3′, 5′- OCH3), 3.03 (m, 2H, 2-H, 2-H), 1.36 (t, J = 7.1 Hz, 3H, CH2CH3). Compound 84, i. e., [4′-O-DEMETHYL-40- [4″- (ETHOXYCARBONYL)-3″-] pyrazolylamino] -4-desoxypodophyllotoxin. Yield 40 %; White solid, mp [152-155 C] [(DEC.) ; ESI] MS: 536 [M-H]. 1H NMR [(CDC13)] [8] 7.32 (s, 1H, 5″-H), 6.66 (s, 1H, 5- H), 6.62 (s, [1H,] 8-H), 6.31 (s, 2H, 2′, 6′-H), 6.01, 6.00 (dd, J = 1. 1 Hz, [2H,-OCH70-),] 5.45 (s, 1H, NH), 5.43 (d, J = 4.9 Hz, [1H,] 4-H), 4.70 (d, J = 4.9 Hz, [1H,] 1-H), 4.68 (br, 1H, [11-H),] 4.36 (br, [1H,] [11-H),] 4.25 (m, 2H, [CH2CH3),] 3.79 (s, 6H, 3′, 5′- [OCH9,] 3.55 (m, 1H, 3-H, ), 3.25 (dd, J = 4.9 Hz, 1H, 2-H, ), 1.35 (t, J = 7.1 Hz, 3H, CH2CH3). Compound 140, i. e., [4′-O-DEMETHYL-4ss-[2″-(3″-(2″‘-CHLORO-4″‘-] pyridinylamino-carbonyl))-pyridinlylamino]-4-desoxypodophyllotoxin. Amorphous, mp > 240 C (dec); ESI MS: 630.0 [(M-1)] [;’H] NMR 6 (400 MHz, [CDC13)] : 8.65 [(1H,] d, J = 2.3 Hz, 3″‘-H of second pyridine), 8.32 [(1H,] d, J = 5.5 Hz, [6″‘-H] of second pyridine), 7.95 [(1H,] dd, J = 2.3, 9.0 Hz, 4″-H of first pyridine), 7.76 [(1H,] d, J = 2.0 Hz, 6″-H of first pyridine), 7.48 [(1H,] dd, J = 2.0, 5.9 Hz, 5″‘-H of second pyridine), 6.79 [(1H,] s, 5-H), 6.56 [(1H,] s, 8-H), 6.50 [(1H,] d, J = 9.0 Hz, 3″-H of first pyridine), 6.34 (2H, s, 2′-H, 6′-H), 5.98 (2H, d d, J = 1. 2,6. 7 Hz,-OCH20-), 5.44 [(1H,] d. [J =] 5.5 Hz, 4-H), 4.63 (1H, d, J = 3.9 Hz, [1-H),] 4.42 (1H, dd, J = 7.0, 9.4 Hz, 113035-H), 3.80 [(1H,] d, J = 2.2, 8.8 Hz, 2-H), 3.80 (6H, s, 3′, 5’-OCH3), 3.50 [(1H,] m, 3-H), 3.03 (1H, br. d, J = 4.7 Hz, 11ss-H).
64987-16-2 Methyl 2-(2-aminothiazol-4-yl)acetate 738059, athiazole compound, is more and more widely used in various fields.
Reference：
Patent; PLANTACEUTICA INC.; WO2004/33423; (2004); A2;,
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