[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](I)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25](C)[CH:26]=O>ClCCl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([N:25]([CH3:26])[CH3:24])[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a sealed tube was added 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (See Example 2, 50 mg, 0.11 mmol, 1.0 equiv) and dimethyl formamide (1 mL). The reaction mixture was stirred at 100° C. After 18 hr, the reaction mixture was cooled to room temperature and diluted with dichloromethane washed with saturated NaHCO3, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 2-(6-dimethylamino-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (32 mg, 80%). 1H NMR (400 MHz, CD2Cl2) δ 8.51 (s, 1H), 8.06 (s, 1H), 7.29-7.36 (m, 5H), 6.21 (bs, 1H), 4.59 (d, J=8.0 Hz, 2H), 3.17 (s, 6H), 2.71 (s, 3H); HRMS (M+H)+=354.13.
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