1,2-Dichloroethane → HCID 23537718, compound

HRID 1792606Notes

Reaction equation

HRID 1792606 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+].[Cl:54][CH2:55][CH2:56]Cl.O>CN(C)C=O>[Cl:54][CH2:55][CH2:56][N:2]([CH3:1])[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:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=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:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:25]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 962WaterHCID 24758Sodium hydrideHCID 23537543HCID 23537543, compound

Product 1

HCID 23537718HCID 23537718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

314 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 8 mL N,N-dimethylformamide, then 21 mg sodium hydride was added thereto and stirred for 20 minutes, and 0.35 mL 1,2-dichloroethane was added thereto and stirred at room temperature for 2 hours. Further, 0.35 mL 1,2-dichloroethane was added thereto and stirred at 60° C. for 24 hours. Water was added to the reaction solution which was then extracted with ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated, and then the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give 325 mg of the title compound as a colorless amorphous.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. stirringstirred at 60° C. for 24 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water and 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-770d9ad2366f4919b3072201ab4766eb
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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