Potassium Hydroxide → HCID 66589194, compound

HRID 1092203Notes

Reaction equation

HRID 1092203 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[C:13]4[CH:14]=[C:15]([NH:20][C@H:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[CH3:22])[C:16]([C:18]#[N:19])=[CH:17][C:12]=4[N:11]=[CH:10]3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-:30].[K+]>CO.OO.O>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[C:13]4[CH:14]=[C:15]([NH:20][C@H:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[CH3:22])[C:16]([C:18]([NH2:19])=[O:30])=[CH:17][C:12]=4[N:11]=[CH:10]3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 66589124HCID 66589124, compound

Product 1

HCID 66589194HCID 66589194, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

1-(5-Cyclopropyl-1H-pyrazol-3-yl)-6-[(S)-1-(4-fluorophenyl)ethylamino]-1H-benzo[d]imidazol-5-carbonitrile (Example 33; 0.30 g, 0.77 mmol) was dissolved in MeOH (10 ml), followed by addition of 25% aqueous KOH solution (0.87 ml, 3.88 mol) and 15 drops of 30% H2O2 solution. The reaction was heated at 75° C. for 48 hours. After cooling, the reaction was diluted with H2O (5 ml). The resulted solid was collected by filtration and dried under vacuum to give the title compound (0.137 g, 44%) as a white solid. NMR (400 MHz) 12.70 (s, 1H), 8.66 (d, J=4.8 Hz, 1H), 8.30 (s, 1H), 8.06 (s, 1H), 8.03 (br, 1H), 7.42 (m, 2H), 7.24 (br, 1H), 7.13 (m, 1H), 6.80 (s, 1H), 6.00 (s, 1H), 4.57 (m, 1H), 1.95 (m, 1H), 1.47 (d, J=6.0 Hz, 3H), 1.02 (m, 2H), 0.74 (m, 2H). MS: Calcd.: 404; Found: [M+H]+ 405.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulted solid was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-80be6b89a4d748b990e76b3cfe956e17
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

Loading…