Pivalic acid → HCID 59272467, compound

Participants

Reaction Conditions

Reaction Steps

Combine 1-(2-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)-4-fluorophenyl)ethanone (0.1 g, 0.21 mmol), 10% trimethylacetic acid in dioxane (2 mL), 2-(methylamino)ethanol (18.2 mg, 0.252 mmol) and silica-supported cyanoborohydride (0.276 g, 0.262 mmol). Heat the reaction mixture at 160° C. for 2 h in a microwave reactor. Add 2-(methylamino)ethanol (0.157 g, 2.1 mmol) and silica-supported cyanoborohydride (0.138 g, 0.131 mmol). Heat the reaction mixture at 160° C. for 4 h in a microwave reactor. Pour the crude reaction mixture onto a strong cation exchange (SCX) (10 g) column. Elute with 2 N methanolic ammonia (40 mL) and concentrate. Purify the residue by normal phase chromatography (0-100% B at 25 mL/minute for 25 minutes on a 12 g silica column, Solvent A: DCM, Solvent B: 10% 2 N methanolic ammonia in DCM) to give the title compound (41 mg, 36%). MS (ES) m/z 536 [M+1]+.

Provenance & Evidence