Triethylamine → HCID 69078363, compound

Participants

Reaction Steps

A solution of methanesulfonyl chloride (0.253 mL, 3.27 mmol) in dichloromethane (10 mL) was added dropwise to a stirred solution of 2-[(aminooxy)methyl]-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 123, 860 mg, 2.97 mmol) and triethylamine (1.24 mL, 8.92 mmol) in dichloromethane (20 mL) at 0° C. After 1 hour, additional methanesulfonyl chloride (0.125 mL in dichloromethane (5 mL)) and triethylamine (0.5 mL) were added. The reaction mixture was stirred for an additional 30 minutes, then was concentrated under reduced pressure to afford a yellow foam. The foam was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 5-15% 1 M NH3 in methanol/dichloromethane) followed by crystallization from methanol/acetonitrile. The crystals were isolated by filtration, washed with acetonitrile, and dried in a vacuum oven to yield 160 mg of N-{[4-amino-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}methanesulfonamide hydrochloride as a white crystals, mp 211-213° C.

Provenance & Evidence