Oxalyl chloride → HCID 69239376, compound

HRID 1726916Notes

Reaction equation

HRID 1726916 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([Cl:52])=[C:34]([N:36]2[CH2:45][C:44]3[C:39](=[N:40][C:41]([S:46]([CH3:49])(=[O:48])=[O:47])=[N:42][CH:43]=3)[N:38]([CH3:50])[C:37]2=[O:51])[CH:35]=1>O1CCCC1.ClCCl>[Cl:52][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:9][CH:10]=3)=[CH:19][CH:18]=2)=[O:21])=[CH:35][C:34]=1[N:36]1[CH2:45][C:44]2[C:39](=[N:40][C:41]([S:46]([CH3:49])(=[O:47])=[O:48])=[N:42][CH:43]=2)[N:38]([CH3:50])[C:37]1=[O:51]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 39226468HCID 39226468, compoundHCID 68700878HCID 68700878, compound

Product 1

HCID 69239376HCID 69239376, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

300 mg of 4′-Morpholin-4-ylmethyl-biphenyl-4-carboxylic acid in 15 ml dry tetrahydrofuran (THF) were treated dropwise with 129 mg oxalyl chloride under cooling with ice. The mixture was subsequently stirred for 20 min at room temperature (RT) before a suspension of 200 mg aniline derivative from example d in 5 ml dichloromethane was added slowly. The mixture was stirred over night and then diluted with 50 ml dichloromethane. Precipitate was filtered off and the filtrate was washed several times with conc. aqueous sodium carbonate solution. The organic phase was dried, evaporated and purified by flash chromatography on silica, using a gradient from dichloromethane to dichloromethane/methanol (60/1) to dichloromethane/methanol/concentrated ammonia (60/1/0.2).

Workup

  1. temperatureunder cooling with ice
  2. additionwas added slowly
  3. stirringThe mixture was stirred over night
  4. filtrationPrecipitate was filtered off
  5. washthe filtrate was washed several times with conc. aqueous sodium carbonate solution
  6. customThe organic phase was dried
  7. customevaporated
  8. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-65db751224bb472f8dd9f474a7b1af1a
Source dataset
uspto-grants-2009_02
Patent number
US07494993B2

Reaction notes

Loading…