Trifluoroacetic acid → HCID 59152452, compound

Participants

Reaction Steps

Combine 4-{5-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (1.67g, 3.10 mmol) with trifluoroacetic acid (2.31 mL, 31.04 mmol) in dichloromethane (20 mL) and stir at RT overnight. Load the mixture onto an SCX column and wash with methanol and dichloromethane. Elute the product with 2M NH3 in methanol and concentrate in vacuo. Chromatograph the residue (silica gel, eluting with 0-10% 2M NH3 in MeOH:dichloromethane) to yield 996 mg (73%) of 2-(4-chloro-phenyl)-6-[6-(piperidin-4-yloxy)-pyridin-3-yl]-6H-thieno[2,3-c]pyridin-7-one. Add ammonium chloride (45 mg, 0.85 mmol) to a solution of the free base (350 mg, 0.80 mmol) in 15 mL of methanol/dichloromethane (1:1) and sonicate the solution until complete dissolution of NH4Cl. Concentrate in vacuo to yield 379 mg (100%) of the title compound. MS/ES m/z (35C1) 438.0 [M+H]+.

Provenance & Evidence