1,2-Dichloroethane → HCID 69069960, compound

Participants

Reaction Conditions

Reaction Steps

Combine 4-fluoro-N-[6-(1-methyl-piperidin-4-yloxy)-pyridin-2-yl]-benzamide hydrochloride (example 161, 365 mg, 1.11 mmol) and 1,2-dichloroethane (10 mL) and add 1-chloroethyl chloroformate (1.20 mL, 11.1 mmol). Heat the reaction to 80° C. for 18 hr. Add additional 1-chloroethyl chloroformate (600 μL, 5.5 mmol) and continue to heat at 80° C. for 5 hr. Cool reaction to ambient temperature and add methanol. Load solution onto an SCX column and wash with methanol. Flush off product with 2 M ammonia in methanol and concentrate in vacuo. Purify by column chromatography (2%-8% 2 M NH3 in methanol/CH2Cl2). Make the hydrogen chloride salt by sonication with one equivalent of ammonium chloride dissolved in methanol to yield of the title compound (115 mg, 29%). Mass spectrum (ion spray): m/z 316.3 (M+1); Analysis calculated for C17H19N3O2FCl.0.5H2O. Theory: C, 56.59; H, 5.59; N, 11.65. Found: C, 56.83; H, 5.38; N, 11.74. mp=251-3° C.

Provenance & Evidence