ChemicalBook CAS DataBase List 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide synthesis

7synthesis methods

Product Name:2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
CAS Number:302964-24-5
Molecular formula:C11H10ClN3OS
Molecular Weight:267.73

2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide can be used as a precursor for the synthesis of dasatinib (D193600), mainly for laboratory research and development processes. It can be synthesized by the ring closure reaction of Carbamimidothioic acid and (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide.

302964-06-3
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2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

302964-24-5
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$9.00/250mg

Yield:302964-24-5 89%

Reaction Conditions:

with trifluoroacetic acid at 25 - 30; for 2 h;

Steps:

2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (9)
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, 89%) [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].

References:

Suresh, Garbapu;Nadh, Ratnakaram Venkata;Srinivasu, Navuluri;Yennity, Durgaprasad [Synthetic Communications,2017,vol. 47,# 17,p. 1610 - 1621] Location in patent:supporting information

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