Acetic Acid → HCID 131729942, compound

Participants

Reaction Steps

Add acetic acid (1.50 g, 2.48 mmol) and formaldehyde (0.20 g, 2.48 mmol, 37% aqueous solution) to a solution of 2-(4-chloro-phenyl)-6-[3-methoxy-4-(pyrrolidine-3-carbonyl)-phenyl]-6H-thieno[2,3-c]pyridin-7-one, trifluoro-acetic acid (0.36 g, 0.62 mmol) in methanol (31 mL). Stir the mixture at RT for 15 min, then add sodium triacetoxyborohydride (0.55 g, 2.48 mmol), and continue to stir the mixture at RT for 2 h. Dilute the mixture with CH2Cl2 (200 mL), wash with saturated NaHCO3, and back extract the aqueous with CH2Cl2 (100 mL). Wash the combined organic phases with water (100 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by filtering with Et2O (100 mL) and water (50 mL). To prepare the HCl salt dissolve the solid in CH2Cl2, and add 1 eq 1M HCl/ether. Allow the solution to stir for 15 min, and concentrate to give 0.16 g (50%) of the title compound. LC-MS/ES m/z (35Cl) 479.0 [M+H]+.

Provenance & Evidence