Ethanol → HCID 53241506, compound

Participants

Reaction Steps

To a mixture of 2-(8-Cyclopropyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde (350 mg, 0.566 mmol) in 40 mL 1:1 absolute ethanol and THF cooled to 0 C was added sodium borohydride (22 mg, 0.566 mmol, 1 eq) and the reaction was stirred for 1 hour at 0 C. The reaction was quenched with water and 2 drops glacial acetic acid, and stirred for 5 min. The mixture was concentrated in vacuo to remove THF and Ethanol, neutralized with a few drops of aqueous saturated sodium bicarbonate, then concentrated to dryness. The residue was loaded directly on an analogix 40 g column using 10% methanol in CH2Cl2, and eluted with a gradient of 5% to 10% methanol in CH2Cl2 to give a solid. Repurification using HPLC gave 200 mg 8-Cyclopropyl-4-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, as a solid, 63% yield.

Provenance & Evidence