Water → HCID 23537542, compound

HRID 1792607Notes

Reaction equation

HRID 1792607 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[S:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[C:22]([C:45]5[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=5)=[N:23][N:24]([C:26]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:25]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:5])=[O:4].[H-].[Na+].[CH3:54][O:55][C:56]1[CH:65]=[CH:64][C:59]([C:60](=[O:63])[CH2:61]Br)=[CH:58][CH:57]=1.O>CN(C)C=O>[CH3:54][O:55][C:56]1[CH:65]=[CH:64][C:59]([C:60](=[O:63])[CH2:61][N:2]([CH3:1])[S:3]([C:6]2[S:7][C:8]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:21]5[C:22]([C:45]6[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=6)=[N:23][N:24]([C:26]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=6)([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:25]=5)[CH:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:9][CH:10]=2)(=[O:5])=[O:4])=[CH:58][CH:57]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 24758Sodium hydrideHCID 23537543HCID 23537543, compound

Product 1

HCID 23537542HCID 23537542, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

50 mg 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thiophen-2-sulfonic acid methylamide (compound in Example 745) was dissolved in 3 mL N,N-dimethylformamide, then 3.1 mg sodium hydride was added thereto and stirred at room temperature for 0.5 hour. Under ice-cooling, a solution of 18 mg 4-methoxyphenacyl bromide in 2 mL N,N-dimethylformamide was added thereto and stirred for 1.0 hour under ice-cooling. Water was added to the reaction solution which was then extracted with ethyl acetate, 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 column chromatography (ethyl acetate/hexane) to give 47 mg of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. stirringstirred for 1.0 hour under ice-
  3. temperaturecooling
  4. extractionwas then extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7cbb69a637aa4f8ab42b59cb7d9ce21f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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