Sodium Bicarbonate → HCID 46215816, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl[6-(2-(methylamino)-6-{(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinyl}-4-pyrimidinyl)-1H-indazol-3-yl]carbamate (530 mg, 0.95 mmol) in CH3OH (15 mL) and conc. HCl (0.5 mL) was heated at 50° C. for a total of 6 hours. The residue was taken up in 5 mL of water, to which was added 5 mL of sat. NaHCO3. The resulting suspension was sonicated, and filtered. The yellow solids collected underwent purification by silica gel column chromatography using elution of gradient 1% A in CHCl3 to 60% A in CHCl3 (A was 200/800/20 CH3OH/CHCl3/NH4OH). Trituration of the residue obtained from the chromatography in MTBE (6 mL), followed by drying under vacuum at 50° C. for 20 hours afforded the title compound (221 mg) as a yellow solid. LC-MS (ES) m/z=457 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 1.33 (d, J=6.8 Hz, 3H), 1.82-1.97 (m, 3H), 2.06-2.16 (m, 1H), 2.57-2.65 (m, 1H), 2.98 (s, 3H), 3.15-3.25 (m, 1H), 6.51 (s, 1H), 7.12 (t, J=7.5 Hz, 1H), 7.34 (t, J=8.1 Hz, 2H), 7.54 (dd, J=8.5, 1.1 Hz, 1H), 7.60 (dd, J=8.6, 1.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 1H), 7.87 (s, 1H).

Provenance & Evidence