Water → HCID 22031967, compound

HRID 1792539Notes

Reaction equation

HRID 1792539 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+].[CH3:55][C:56]1[C:61]([OH:62])=[CH:60][CH:59]=[CH:58][N:57]=1.O>CN(C)C=O>[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:47]=[CH:48][C:49]([F:52])=[CH:50][CH:51]=5)=[N:24][N:25]([C:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)([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)[CH:26]=4)[CH:20]=[CH:21][C:8]=3[N:7]=[C:6]2[O:62][C:61]2[C:56]([CH3:55])=[N:57][CH:58]=[CH:59][CH:60]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707192-Methylpyridin-3-olHCID 22031275HCID 22031275, compound

Product 1

HCID 22031967HCID 22031967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 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 2 mL N,N-dimethylformamide, then 6.8 mg sodium hydride was added thereto and stirred for 20 minutes, and 3 mL 2-methyl-3-pyridinol was added thereto and stirred at 80° C. for 3 hours. Water was added thereto, and the reaction solution was extracted with ethyl acetate, and the organic layer was washed with water and 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-[(2-methyl-3-pyridyl)oxy]-1H-benzo[d] imidazole. This product was subjected to deprotection of the trityl group by the same method as in Example 84 and then purified by NAM silica gel chromatography (ethyl acetate/methanol), to give 6 mg of the title compound as colorless crystals.

Workup

  1. stirringstirred at 80° C. for 3 hours
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f6bf2872e08f4d34b21a5120fce59da9
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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