Dasatinib intermediates

China Manufacturer 302964-24-5 | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Categories: Anti-tumor intermediates, Pharmaceutical Intermediates Tags: Anti-tumor intermediates, Dasatinib Intermediates

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product Name	2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
Synonyms	2-Amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide; Dasatinib’s intermediate; 5-thiazolecarboxamide, 2-amino-N-(2-chloro-6-methylphenyl)-; 2-Amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide; 2-amino-N-(2-chloro-6-methyl-phenyl)-thiazole-5-carboxamide; 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
Molecular Formula	C₁₁H₁₀ClN₃OS
Molecular Weight	267.73
InChI	InChI=1/C15H17N3O/c1-9-6-10(2)14(11(3)7-9)18-15(19)12-4-5-17-8-13(12)16/h4-8H,16H2,1-3H3,(H,18,19)
CAS Registry Number	302964-24-5
Molecular Structure
Density	1.474g/cm³
Boiling point	362°C at 760 mmHg
Refractive index	1.714
Flash point	172.7°C
Vapour Pressur	1.99E-05mmHg at 25°C
Uses	2-Amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide, is a precursor in the synthesis of Dasatinib (D193600), a protein tyrosine kinase inhibitor, and also for 2-Amino-thiazole-5-carboxylic Acid Phenylamide Derivatives, used as potent and selective anti-tumor drugs.
Synthesis	2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is synthesised using Tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-YL)carbamate as a raw material by chemical reaction. The specific synthesis steps are as follows: To the stirred solution of trifluoroacetic acid (TFA) (250.0 mL) added tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)carbamate 23 (25.0 g, 0.07 mol) and stirred for 2h at 25-30°C. Reaction completion was confirmed by TLC, distilled the TFA and the residue was diluted with ethyl acetate (EtOAc),(250.0 mL). Ethyl acetate layer was washed with saturated NaHCO3 solution (2 X 25.0 mL), water, followed bysaturated NaCl solution (125.0 mL). Ethyl acetate layer was dried over Na2SO4 and concentrated. The residual mass on treatment with methyl tert-butyl ether (250.0) gave 9 (16.2 g, 89percent) [11].IR (KBr, cm-1): 3382.4, 3284.85 (N-H), 1627.02 (C=O), 1644; 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm(J, Hz): 9.63 (s, 1H, thiazole-H), 7.86 (s, 1H), 7.60 (s, 2H, -NH2), 7.38 (dd, 1H, J =7.5, 4.02, Ar-H), 7.20-7.22 (m,2H, J =7.5, Ar-H), 2.20 (s, 3H, Ar-CH3); 13C NMR spectrum (100 MHz, DMSO-d6), δ, ppm: 172.2, 159.6, 143.2,138.9, 133.7, 132.5, 129.0, 128.0, 127.0, 120.7 and 18.3; MS (ESI) m/z 268.0 [M + H] + [11].
Raw materials	2-Chloro-6-methylaniline–>N-TRIPHENYLMETHYLTHIOUREA–>Ethyl 2-aminothiazole-5-carboxylate–>Dasatinib–>(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide–>3-Ethoxyacryloyl chloride

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