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| | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Basic information |
| Product Name: | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide | | Synonyms: | Dasatinib IMpurity 2;2-AMino-N-(2-chloro-6-Methylphenyl)thiazole-5-carboxiMide);2-Amino-5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazole, 2-Amino-5-[(6-chloro-o-tolyl)carbamoyl]-1,3-thiazole;5-ThiazolecarboxaMide,2-aMino-N-(2-chloro-6-Methylphenyl);Dasatinib Int N-2;2-AMino-N-(2-chloro-6-Meth;2-AMino-N-(2-chloro-6-Methylphenyl)-5-thiazolecarboxaMide;2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide | | CAS: | 302964-24-5 | | MF: | C11H10ClN3OS | | MW: | 267.73 | | EINECS: | 1806241-263-5 | | Product Categories: | Dasatinib;API intermediates | | Mol File: | 302964-24-5.mol |  |
| | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Chemical Properties |
| Melting point | 208.0 to 212.0 °C | | Boiling point | 362.0±37.0 °C(Predicted) | | density | 1.474±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | DMSO (Slightly), Methanol (Sparingly) | | form | powder to crystal | | pka | 11.09±0.70(Predicted) | | color | White to Light yellow | | InChI | InChI=1S/C11H10ClN3OS/c1-6-3-2-4-7(12)9(6)15-10(16)8-5-14-11(13)17-8/h2-5H,1H3,(H2,13,14)(H,15,16) | | InChIKey | VVOXTERFTAJMAA-UHFFFAOYSA-N | | SMILES | S1C(C(NC2=C(C)C=CC=C2Cl)=O)=CN=C1N | | CAS DataBase Reference | 302964-24-5(CAS DataBase Reference) |
| | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Usage And Synthesis |
| 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].
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| | 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Preparation Products And Raw materials |
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