Ethyl Acetate → HCID 178508364, compound

Participants

Reaction Steps

To a solution of 6-{7-amino-4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-2-yl}-2,3-dihydro-1H-isoindol-1-one in THF (2.4 mL) was added tetra-n-butylammonium fluoride (1.0 M in THF, 2.4 mL, 2.4 mmol). After 4 h, the reaction was diluted into EtOAc and washed with sodium bicarbonate and water. The aqueous layer was concentrated. The residual solid was rinsed with MeOH and EtOAc thoroughly, then purified by ISCO chromatography (0 to 10% 7 N NH3/MeOH:EtOAc) to afford 1.5 mg (3%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.44 (s, 1H), 8.34 (d, J=7.8 Hz, 1H), 8.16 (s, 1H), 7.92 (d, J=5.3 Hz, 2 H), 7.76 (d, J=8.1 Hz, 1H), 7.63 (s, 1H), 4.56-4.58 (m, 2H), 4.23-4.34 (m, 1H), 3.67-3.78 (m, 1H), 2.11-2.25 (m, 4H), 1.97-2.08 (m, 2H), 1.54 (m, 2H); MS (ESI): 430.17 [M+H]+; HPLC tR=0.90 min (TOF: polar—3 min).

Provenance & Evidence