Methanesulfonyl chloride → [4-Amino-2-(1-methanesulfonylpiperidin-4-ylamino)thiazol-5-yl]-(2,3-difluoro-6-methoxyphenyl)methanone

Participants

Reaction Steps

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(2,3-difluoro-6-methoxy-phenyl)methanone methanone (0.05 g, 0.14 mmol) (Example 8) was treated with methanesulfonyl chloride in a manner similar to Example 9 except that diisopropylethyl amine was additionally used as a catalyst to give 50 mg (90% yield) of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)thiazol-5-yl]-(2,3-difluoro-6-methoxyphenyl)methanone. 1H NMR (DMSO−d6, 300 MHz) δ1.57 (m, 2H, CH2), 1.92 (m, 2H, CH2), 2.85 (m, 5H, SCH3 & NCH2), 3.53 (m, 2H, NCH2), 3.6-4.0 (broad,1H, CH), 3.88(s, 3H, OCH3), 6.72 (m,1H, Aromatic), 7.42 (m,1H, Aromatic), 7.6 (2× brd, 1H, NH), 7.8 (brd, 1H, NH), 7.99 (m, 1H, Aromatic), 9.0 (brd, 1H, NH). LR/LC/MS: (M+H): compatible with 446. Ki CDK1=0.001 μM; Ki CDK2=0.001 μM; Ki CDK4=0.002 μM.

Provenance & Evidence