Sodium hydride → HCID 57937400, compound

Participants

Reaction Conditions

Reaction Steps

N-Ethyl-1H-pyrrole-3-carboxamide (50 mg, 0.36 mmol) was dissolved in THF (3 mL) and the solution was cooled down to 0° C. NaH (72 mg, 60%, 1.8 mmol) was then added and the reaction mixture was allowed to warm to room temperature and stirred for 1 hour at room temperature. The reaction mixture was cooled down to 0° C. again and 2-(1,1-difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (114 mg, 0.30 mmol) was added slowly, allowing the reaction to warm to room temperature and stirred for 3 hours. The reaction mixture was slowly added to a stirring mixture of EtOAc and NH4Cl at −20° C., which was extracted with EtOAc, washed with NH4Cl, water then brine. Concentrated under vacuum and purified by LCMS using high pH column 40-70% acetonitrile gradient to afford the title compound as a white solid. Yield: 25 mg (17%). 1H NMR (400 MHz, METHANOL-D4) δ 1.14 (t, J=7.23 Hz, 3 H), 1.32-1.41 (m, 2 H), 1.40-1.43 (m, 3 H), 1.43-1.53 (m, 2 H), 2.25 (t, J=19.53 Hz, 5H), 3.89 (dd, J=11.52, 2.54 Hz, 2 H), 4.37 (d, J=7.62 Hz, 2 H), 6.65 (s, 1 H), 7.31 (t, J=2.34 Hz, 1 H), 7.82 (s, 1 H), 7.88-7.94 (m, 1 H), 7.95-8.01 (m, 1 H), 8.40 (s, 1 H); MS (APPI) (M+H)+=481.2; Anal. Calc. for C22H26F2N4O4S+0.4 TFA: C, 52.05; H, 5.06; N, 10.65. Found: C, 52.41; H, 3.78; N, 10.41.

Provenance & Evidence