Sodium Bicarbonate → HCID 178517301, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-pyridine-3-sulfonic acid [(6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl]-amide (example 15) (100 mg, 0.21 mmol) was added to concentrated hydrochloric acid (10 mL, 12 M), the mixture was stirred for 24 h at 100° C. To the mixture was added sat. NaHCO3 to adjust to pH=8. Then extracted with ethyl acetate (15 mL×2), dried over anhydrous sodium sulfate and concentrated. The residue was directly purified by pre-TLC (dichloromethane:MeOH=100:1) to yield 20 mg (21%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 12.0 (bs, 1H) 8.22-8.19 (m, 1 Hz), 7.85-7.80 (m, 1H), 7.46-7.41 (m, 2H), 7.11-7.08 (m, 2 Hz), 6.49-6.41 (m, 2H), 4.09-3.91 (m, 4H), 3.63-3.61 (m, 1H), 3.04-3.01 (m, 1H), 2.22-2.20 (m, 1H), 1.64-1.62 (m, 1H); LC-MS: 459.0 [M+1]+.

Provenance & Evidence