Cyclopentanesulfonyl chloride → HCID 66547934, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-N,N-dimethyl-4-(2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridin-6-ylamino)benzamide (Example 127, 25 mg, 0.063 mmol) was dissolved in dry DMF. The solution was degassed and a solution of sodium bis(trimethylsilyl)amide (0.1 ml of a 1M solution in THF, 1 mmol) was added. After 20 minutes reaction, cyclopentyl sulfonyl chloride (17 mg, 0.1 mmol) was added and the reaction heated to 60° C. for 3 hours. The reaction was cooled to room temperature and diluted with ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulphate and concentrated in vacuum. The crude product was purified by silica gel column chromatography eluting with 5% methanol in ethyl acetate to afford the title compound as white foam (6 mg, 18%). 1H-NMR (500 MHz, d6-DMSO): δ 1.5 (m, 2H), 1.6 (m, 2H), 1.75 (m, 4H), 2.97 (s, 6H), 3.11 (m, 1H), 3.89 (s, 3H), 6.77 (s, 1H), 7.33 (dd, J=2 Hz, 8.6 Hz, 1H), 7.48 (d, J=2 Hz, 1H), 7.68 (s, 1H), 7.76 (s, 1H), 8.01 (s, 1H), 8.12 (d, J=8.6 Hz, 1H), 8.51 (s, 1H), 8.7 (s, 1H). ESI-HRMS Found 527.1621, calculated for C25H27ClN6O3S (M+H+): 527.1627. MPS1 IC50 (uM): 0.092

Provenance & Evidence