5-bromo-4-trifluoromethyl-thiazole-2-ylamine

To a stirred solution of Example 183 5-Bromo-N-[5-bromo-4-(trifluoromethyl)thiazol-2-yl]-2-hydroxybenzamide (Comopund No. 182). Using 5-bromosalicylic acid and A solution of 5-bromo-4- (trifluoromethyl)thiazol-2-amine above in step b (3.53 g, 15.9 mmol, 1.0 equiv) and 1, 1, 1-trifluoro-2-(4- mercaptophenyl) propan-2-ol (3.93 g, 15.9 mmol, 1.0 equiv) in DMF (30 mL) was treated at 0 C with CuI (3.03 g, 15.9 mmol, 1.0 equiv) and K2C03 (6.06 g, 47.7 mmol, 3.0 equiv) successively. After being stirred at 0 C for 0.5 h and at 25 C for 5 h, the reaction mixture was diluted (EtOAc), washed (3 x brine), dried (Na2S04) and concentrated under reduced pressure. Purification of the residue by flash chromatography (Si02, 20-40% EtOAc/Hexane, gradient elution) gave 1.87 g of the product as a yellow solid (4.83 mmol).Example 6 N-(5-Bromo-4-trifluoromethylthiazol-2-yl)-3, 4-dicloro-benzamide; A solution of 4- (trifluoromethyl)thiazol-2-amine above in step a (3.01 g, 17.9 mmol, 1.0 equiv) and acetic acid (2.1 mL) in CH3CN (21 mL) was treated with N-bromosuccinimide (3.50 g, 19.7 mmol, 1.1 equiv) at 0 °C. After being stirred at 0 °C for 1 h and at 25 °C for 1 h, the reaction mixture was diluted (CH2CI2), washed (saturated aqueous NaHC03 and brine), dried (Na2S04) and concentrated under reduced pressure. Purification of the residue by flash chromatography (Si02, 20-30percent EtOAc/Hexane, gradient elution) gave 4.05 g of the product as a brown solid (16.3 mmol).To a stirred solution of 4-trifluoromethyl-thiazole-2-ylamine (0.2 g; 1.2 mmol) in acetic acid (0.14 mL) and acetonitrile (1.4 mL) at 0 °C was added N- bromosuccinimide (0.23 g, 1.3 mmol). The reaction mixture was warmed to room temperature over 17 h. The reaction was diluted with methylene chloride, washed with saturated aHC03, dried, filtered and concentrated under vacuum to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 20percent to give the product.LCMS: >98percent (at) 214 nm, RT = 2.30 min; m/z 249 [M+H] .

Molecular Weight:247.04
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Exact Mass:245.90742
Monoisotopic Mass:245.90742
Topological Polar Surface Area:67.2
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes