Trifluoroacetic acid → HCID 69585732, compound

Participants

Reaction Steps

2,3-O-(S)-Isopropylidene-L-glyceraldehyde (98 mg, 0.75 mmol) and potassium acetate (75 mg, 0.75 mmol) were added to a solution of N-{(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl}-5-chloro-1H-indole-2-carboxamide (Method 5, 328 mg, 0.75 mmol) in MeOH (10 mL). The reaction was stirred at ambient temperature for approximately 5 mins then macroporous triethylammonium methyl polystyrene cyanoborohydride (352 mg, 0.9 mmol) was added and the reaction stirred at ambient temperature for a further 5 h. The reaction was then filtered and the volatiles were removed by evaporation under reduced pressure to 5-chloro-N-[(1R,2R)-1-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-2,3-dihydro-1H-inden-2-yl]-1H-indole-2-carboxamide which was used crude in the next stage. TFA (3 mL) was added to a solution of 5-chloro-N-[(1R,2R)-1-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-2,3-dihydro-1H-inden-2-yl]-1H-indole-2-carboxamide (100 mg, 0.23 mmol) in DCM (10 mL) and the reaction was stirred at ambient temperature for 24 h. The volatiles were removed by evaporation under reduced pressure to afford the title compound (90 mg, 100%) as a white solid.

Provenance & Evidence