Water → HCID 22031842, compound

HRID 1792536Notes

Reaction equation

HRID 1792536 reaction equation
C(S([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:9]2[CH:18]=[C:19]([C:22]3[C:23]([C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=4)=[N:24][N:25]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:26]=3)[CH:20]=[CH:21][C:8]=2[N:7]=1)(=O)=O)C.[H-].[Na+].O.[C:56](OCC)(=[O:58])C>O1CCCC1.CO>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[C:9]3[CH:18]=[C:19]([C:22]4[C:23]([C:46]5[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=5)=[N:24][N:25]([C:27]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:26]=4)[CH:20]=[CH:21][C:8]=3[N:7]=[C:6]2[O:58][CH3:56])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 22031275HCID 22031275, compound

Product 1

HCID 22031842HCID 22031842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg 2-(ethylsulfonyl)-1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazole obtained in Example 138 was dissolved in 0.5 mL tetrahydrofuran and 3 mL methanol, then 28 mg sodium hydride was added thereto, and the mixture was heated for 3 hours under reflux under nitrogen atmosphere. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and the organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give 1-(4-fluorophenyl)-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-2-methoxy-1H-benzo[d]imidazole. This product was subjected to deprotection of the trityl group in the same manner as in Example 84 and then purified by NAM silica gel chromatography (ethyl acetate/methanol), to give 18 mg of the title compound as colorless crystals.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux under nitrogen atmosphere
  3. temperatureAfter the reaction mixture was cooled
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d201edef8d884917a5cf9d2b6e8988bb
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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