Sodium Hydroxide → HCID 67271565, compound

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([N:12]3[C:16](N)=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]3)[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.[OH-:22].[Na+].Cl[C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:26]>CCOC(C)=O>[C:18]([C:14]1[CH:15]=[C:16]([C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:26])[N:12]([C:8]2[CH:7]=[C:6]([C:4]3[CH:3]=[N:2][N:1]([C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:22])[CH:5]=3)[CH:11]=[CH:10][CH:9]=2)[N:13]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Procedure

1-(3-(1H-pyrazol-4-yl)phenyl)-3-t-butyl-1H-pyrazol-5-amine (160 mg, 0.57 mmol) in EtOAc (3 mL) was cooled to 0° C. and treated with 1M NaOH (0.85 mL, 0.85 mmol) and isopropenyl chloroformate (0.080 mL, 0.74 mmol). The reaction was allowed to warm to RT overnight. The organic layer was washed with saturated NaHCO3, brine, dried (Na2SO4) and was concentrated to a film, which was dissolved in Et2O (5 mL) and the solution was lowed to stand overnight. The resultant crystals were collected, washed with Et2O and dried in vacuo to provide prop-1-en-2-yl 4-(3-(3-t-butyl-5-((prop-1-en-2-yloxy)carbonyl)-1H-pyrazol-1-yl)phenyl)-1H-pyrazole-1-carboxylate (193 mg, 75% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.73 (brs, 1H), 8.96 (d, J=−0.7 Hz, 1H), 8.46 (d, J=0.7 Hz, 1H), 7.87 (t, J=1.7 Hz, 1H), 7.81 (dt, J=8.2, 1.3 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.41 (brd, J=7.9 Hz, 1H), 6.34 (s, 1H), 5.02 (s, 2H), 4.66 (brs, 1H), 4.57 (brs, 1H), 2.06 (s, 3H), 1.76 (brs, 3H), 1.30 (s, 9H). MS (ESI) m/z: 450.2 (M+H+).