Hydrazine hydrate (1:1) → HCID 118207806, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL pear flask were added 2-amino-4-(((S)-1-(6-((S)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrile (20 mg, 0.037 mmol) and hydrazine monohydrate (0.081 mL, 1.7 mmol) in ethanol (1 mL). The mixture was heated to 65° C. for 4 hours. The mixture was diluted with acetonitrile and was then directly purified by preparative HPLC (basic mode, 25-45% ACN/water gradient). The product-containing fractions were combined and lyophilized to give the title compound as a light brown solid (6.9 mg, 46%). The absolute configuration of the stereocenter on the piperidine ring was not determined, but was assigned the opposite configuration of EXAMPLE 4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.56 (m, 3H), 1.84-1.96 (m, 1H), 2.01-2.12 (m, 2H), 2.14-2.26 (m, 2H), 2.31 (s, 4H), 2.57 (d, J=4.55 Hz, 2H), 2.89-2.99 (m, 1H), 3.43-3.51 (m, 1H), 3.59-3.67 (m, 1H), 3.78-3.85 (m, 3H), 6.27 (s, 1H), 6.53-6.56 (m, 1H), 7.43-7.47 (m, 1H), 7.88 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C21H27N9, 406. found 406.

Provenance & Evidence