4-Methylmorpholine → HCID 67003306, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-chloro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzoic acid (Example 16C) (100 mg, 0.235 mmol) in N,N-dimethylformamide (1.17 mL) was added 1-methylpiperazine (78 μl, 0.704 mmol), 4-methylmorpholine (71.2 mg, 0.704 mmol), hydroxybenzotriazole (53.9 mg, 0.352 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (67.5 mg, 0.352 mmol). The solution was heated to 45° C. for 3 hours. The reaction was cooled to room temperature and diluted with dimethyl sulfoxide (1 mL). The resulting solution was purified by reverse phase high performance liquid chromatography (RP HPLC, 19×150 mm Atlantis Prep T3 OBD 5 m column, eluting with a gradient of 5% B in A to 75% B in A over 25 minutes, wherein A is water containing 0.1% v/v trifluoroacetic acid and B is acetonitrile containing 0.1% v/v trifluoroacetic acid) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.67 (bs, 1H), 8.37 (s, 1H), 8.28 (s, 1H), 8.10-8.05 (m, 2H), 7.51-7.44 (m, 2H), 7.17 (s, 1H), 6.68 (s, 1H), 3.76-3.48 (m, 4H), 2.69-2.58 (m, 2H), 2.47-2.25 (m, 6H), 2.20 (s, 3H), 2.05-1.91 (m, 2H); MS ESI(+) m/z 508.1 [M+H]+.

Provenance & Evidence