Potassium Carbonate → HCID 178461921, compound

HRID 243307Notes

Reaction equation

HRID 243307 reaction equation
[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]3[CH:24]=[C:25]([C:28]#[N:29])[CH:26]=[CH:27][C:15]=3[N:14]=2)[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.C(=O)([O-])[O-:31].[K+].[K+]>CS(C)=O.O.OO.CCOC(C)=O>[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]3[CH:24]=[C:25]([C:28]([NH2:29])=[O:31])[CH:26]=[CH:27][C:15]=3[N:14]=2)[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

7

Reactant 2

HCID 11430Potassium Carbonate2×HCID 178461920HCID 178461920, compound

Product 1

HCID 178461921HCID 178461921, compoundYield 168.5%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 784Hydrogen PeroxideSolvent2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(1-(9H-purin-6-ylamino)ethyl)-1-phenyl-1H-benzo[d]imidazole-6-carbonitrile 122 (70 mg, 0.18 mmol) in DMSO (2 mL) was added potassium carbonate (10 mg, 0.07 mmol) followed by hydrogen peroxide (30%, 0.2 mL). After 1 h stirring, additional potassium carbonate (10 mg, 0.07 mmol) in water and hydrogen peroxide 90.2 mL) were added and stirring was continued for 1 h. The solution was then diluted with water (30 mL) and EtOAc was added. A precipitate formed and was filtered off affording 137 as a white solid (47 mg, 64%). LCMS: RT 2.41 min [M+H]+ 399.1. 1H NMR (DMSO, 400 MHz): δ 8.20-8.07 (2H, m), 8.03-7.92 (2H, m), 7.81 (1H, d, J=9.19 Hz), 7.76-7.50 (6H, m), 7.24 (1H, s), 5.51 (1H, bs), 1.58 (3H, d, J=6.84 Hz)

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. additionwas added
  4. customA precipitate formed
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-6a2e44a106ac4e57bfc174a849aeefc3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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