Hydrochloric Acid → HCID 58869117, compound

Participants

Reaction Steps

The preparation of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate is described in Parts A-F of Example 14. A solution of 4M hydrochloric acid in dioxane (1.8 mL, 7.2 mmol, 20 eq) is added to a solution of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate (175 mg, 0.36 mmol, 1.0 eq) in dichloromethane (4 mL) and stirred at ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the resulting crude material was dissolved in 1-methyl-2-pyrrolidinone (NMP) (4 mL) and cooled to −8° C. Triethylamine (0.500 mL, 10 eq) and acetic anhydride (0.034 mL, 0.36 mmol) were sequentially added dropwise to the reaction mixture and stirred for 1 hour. The crude reaction mixture was concentrated reduced pressure at 70° C. The residue was partitioned between saturated aqueous sodium carbonate and chloroform and the phases were separated. The aqueous phase was back-extracted with chloroform and the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford crude material. The material was purified by column chromatography on a BIOTAGE HORIZON High-Performance Flash Chromatography instrument (silica gel, eluting with 10-50% CMA in chloroform) and trituration with chloroform/ethyl acetate. The resulting material was filtered and washed with ethyl acetate and dried under high vacuum to afford 0.025 g of N-[4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N-hydroxyacetamide as a white powder, mp 164.0-166.0° C. MS (APCI) m/z 334 (M)+; Anal. Calcd for C17H27N5O2.0.05CHCl3 C, 60.34; H, 8.03; N, 20.64. Found: C, 60.05; H, 7.97; N, 20.43.

Provenance & Evidence