Formaldehyde → HCID 59285260, compound

Participants

Reaction Steps

Acetic acid (3 drops) was added to a mixture of N-cyclopropyl-3-[2-(cyclopropylmethyl)-1-oxo-4-(piperazin-1-ylsulfonyl)-1,2-dihydroisoquinolin-6-yl]-5-fluoro-4-methylbenzamide (Example 47d, 0.047 g) and paraformaldehyde (7.9 mg) in 1,2-dichloroethane (1 mL). The mixture was stirred at room temperature overnight then sodium triacetoxyborohydride (18.5 mg) was added and the reaction stirred at room temperature for 1 h. DCM (10 mL) was added and the solution washed with water (3×10 mL). The organics were dried (MgSO4), filtered and concentrated under reduced pressure then purified by preparative HPLC (Xbridge column using a 95-5% gradient of aqueous trifluoroacetic acid in acetonitrile) then evaporated to dryness. The product was passed through an ion exchange column (StratoSpheres TM SPE PL-HCO3 MP SPE by Polymer Laboratories, eluting with methanol), to give, after triturating with diethyl ether, the title compound (0.032 g) as a white solid.

Provenance & Evidence