5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amine → 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-propionamide
반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([NH2:12])=[N:11][C:6]2=[CH:5][CH:4]=1.[CH:13]1([CH2:18][CH:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:20](Cl)=[O:21])[CH2:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1>[CH:13]1([CH2:18][CH:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:20]([NH:12][C:10]2[S:9][C:7]3[C:6]([N:11]=2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=3)=[O:21])[CH2:17][CH2:16][CH2:15][CH2:14]1참가 물질
4
실험 절차
To a solution of the title A compound, 5-methoxy-thiazolo[5,4-b]pyridin-2-ylamine (1.22 mmol, 222 mg) in 3 mL of pyridine at 0° C. is added 3-cyclopentyl-2-(4-methansulfonyl-phenyl)-propionyl chloride (1.02 mmol, prepared as described for the preparation of the title C compound in Example 1). The reaction is allowed to warm to RT over 12 h, then evaporated and the residue is partitioned between MTBE and aqueous 0.1 N HCl. The organic solution is washed with water, saturated aqueous NaHCO3 and brine, dried and evaporated to an oil. Chromatography over silica affords 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-propionamide; 1H NMR δ 9.7 (s, 1H), 7.85 (m, 3H), 7.38 (d, J=8, 2H), 6.83 (d, J=8, 1H), 4.05 (s, 3H), 3.63 (t, J=7.5, 1H); 3.09 (s, 3H), 2.2 (m, 1H), 1.1-1.9 (m, 10H); e/z (ES) 460 (M+1, 100%).