Sodium Hydroxide → HCID 58015088, compound

Participants

Reaction Steps

To a mixture of 0.051 g (0.114 mmole) of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-22), 0.0433 g (0.114 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 2.5 mL of dichloromethane, 0.05 mL of triethylamine was added followed by 0.0162 g (0.114 mmole) of 3-piperidin-1-yl-propylamine. After 2 hours, 6 mL of dichloromethane, 4 mL of water and 0.2 mL of 1 M sodium hydroxide was added. The dichloromethane layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-methanol-ammonium hydroxide (91:9:0.75) to give 0.0431 g of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(3-piperidin-1-yl-propyl)-benzamide (I-84).

Provenance & Evidence