[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([OH:9])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C=O.ClCCl>[CH2:40]([NH:47][C:7]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])=[O:9])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1To a solution of 4-methylthiazole-5-carboxylic acid (5.00 g, 34.92 mmol) in anhydrous N,N-dimethylformamide (75 mL) was added 1-hydroxybenzotriazole (5.66 g, 41.91 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (8.04 g, 41.91 mmol), N,N-diisopropylethylamine (18.23 mL, 104.76 mmol) and benzylamine (4.57 mL, 41.91 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (100 mL) and washed with saturated aqueous sodium bicarbonate solution (55 mL) and brine (45 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (35-45% ethyl acetate in hexanes) to afford N-benzyl-4-methylthiazole-5-carboxamide as a white solid (4.85 g, 60%): 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 7.36-7.33 (m, 5H), 6.17 (br s, 1H), 4.61 (d, J=6.0 Hz, 2H), 2.72 (s, 3H); MS (ES+) m/z 233.2 (M+1).
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