Ammonium Chloride → HCID 53353203, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-N-(3-chloro-1-cyclopropyl-1H-pyrrolo[3,2-c]pyridin-6-yl)benzamide (20 mg, 0.040 mmol) was added THF (800 μA). At room temperature, TBAF (1.0M solution in THF, 50 μl) was added. The mixture was heated to 60° C. for 1 hr. After reaction was completed, 2 ml saturated NH4Cl was added and the mixture was extracted with EtOAc (3×2 ml). Organic layers were combined, dried, filtered and concentrated. The crude product was purified by preparatory HPLC (TFA mode, 20-45% ACN in water). Product containing fractions were combined, and then extracted with EtOAc to remove residual TBAF to give the title compound as a white solid (13 mg, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98-1.05 (m, 1H) 1.05-1.12 (m, 1H) 1.26 (d, J=1.52 Hz, 7H) 3.44-3.55 (m, 3H) 4.77 (br. s., 1H) 7.50 (dd, J=8.59, 2.27 Hz, 2H) 7.62 (d, J=6.06 Hz, 1H) 7.96-8.05 (m, 2H) 8.34 (d, J=1.01 Hz, 1H) 8.51 (d, J=1.01 Hz, 1H) 8.61 (d, J=1.01 Hz, 1H) 8.57 (d, J=0.76 Hz, 1H) 10.64 (d, J=9.09 Hz, 1H); ESI-MS: m/z 384 (M+H)+.

Provenance & Evidence