N-methyl-2-pyrrolidone → N-(2-methyl-1,3-benzothiazol-5-yl)-2-((7H-pyrrolo[2,3-d]pyrimidin-4-ylmethyl)amino)-3-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-N-(2-methyl-benzothiazol-5-yl)-nicotinamide (109 mg, 0.38 mmol) was dissolved in t-BuOH (1 mL), then added C-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-methylamine dihydrochloride (126 mg, 0.57 mmol) and DIEA (132 μL, 0.76 mmol). The reaction was heated at 100° C. for 21 h. The t-BuOH was replaced with NMP (0.5 mL), then additional C-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-methylamine dihydrochloride (42 mg, 0.19 mmol) and DIEA (0.15 mL, 0.874 mmol) were added and the mixture was heated at 120° C. for another 21 h. The mixture was diluted with EtOAc. A precipitate formed and was collected by decanting off the EtOAc. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2) to give N-(2-methyl-1,3-benzothiazol-5-yl)-2-((7H-pyrrolo[2,3-d]pyrimidin-4-ylmethyl)amino)-3-pyridinecarboxamide as a light yellow solid. MS m/e 416.1 (M+H)+ Calc'd for C21H17N7OS—415.4.

Provenance & Evidence