Water → HCID 23537789, compound

HRID 1792581Notes

Reaction equation

HRID 1792581 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:13]2[CH:14]=[C:15]([C:18]3[C:19]([C:42]4[CH:47]=[CH:46][C:45]([NH:48][C:49]([N:51]5[CH2:56][CH2:55][O:54][CH2:53][CH2:52]5)=[O:50])=[CH:44][CH:43]=4)=[N:20][N:21]([C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:22]=3)[CH:16]=[CH:17][C:12]2=[N:11][CH:10]=1.[CH3:57]I.O>CN(C)C=O.C(OCC)(=O)C>[CH3:57][N:48]([C:45]1[CH:44]=[CH:43][C:42]([C:19]2[C:18]([C:15]3[CH:16]=[CH:17][C:12]4[N:13]([C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=5)=[CH:10][N:11]=4)[CH:14]=3)=[CH:22][N:21]([C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:20]=2)=[CH:47][CH:46]=1)[C:49]([N:51]1[CH2:52][CH2:53][O:54][CH2:55][CH2:56]1)=[O:50]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23537747HCID 23537747, compound

Product 1

HCID 23537789HCID 23537789, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

6 mg sodium hydride was suspended in 2 mL N,N-dimethylformamide, then 3 mL of 64 mg morpholine-4-carboxylic acid {4-[4-(3-pyridin-2-ylimidazo[1,2-a]-pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]phenyl}amide (compound in Example 357) in N,N-dimethylformamide was added thereto under ice-coolingd water in a stream of nitrogen, and the reaction solution was returned to room temperature and stirred for 20 minutes. 7 μL methyl iodide was added thereto under ice-cooling and stirred for 20 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 55 mg of the title compound as a colorless amorphous.

Workup

  1. customwas returned to room temperature
  2. temperatureunder ice-cooling
  3. stirringstirred for 20 minutes
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dc1802b6f513472bae8855d9e31bf0c9
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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