N,N-Dimethylglycine → HCID 67003696, compound

Participants

Reaction Steps

A solution of 4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-fluoroaniline (Example 60B) (68 mg, 0.148 mmol) and dimethyl glycine (15.3 mg, 0.148 mmol) in N,N-dimethylformamide (0.5 mL) was treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67.6 mg, 0.178 mmol) and 4-(dimethylamino)pyridine (1.8 mg, 0.015 mmol). The reaction was stirred for 16 hours at ambient temperature. The reaction was treated with more O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67.6 mg, 0.178 mmol) and 4-(dimethylamino)pyridine (18.1 mg, 0.148 mmol), and the reaction was stirred another 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water, saturated sodium bicarbonate solution, and brine. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 1 to 5% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 544.1 [M+H]+.

Provenance & Evidence