Dimethyl Sulfoxide → HCID 86597671, compound

HRID 1951669Notes

Reaction equation

HRID 1951669 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:49])([F:48])[C:13]1[CH:14]=[C:15]([C:23]([CH3:47])([CH3:46])[C:24]([N:26]([C:28]2[CH:29]=[N:30][C:31]([NH:41][CH2:42][CH:43]([OH:45])[CH3:44])=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[CH3:27])=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.C(N(C(C)C)C(C)C)C>ClCCl>[F:49][C:12]([F:11])([F:48])[C:13]1[CH:14]=[C:15]([C:23]([CH3:46])([CH3:47])[C:24]([N:26]([C:28]2[CH:29]=[N:30][C:31]([NH:41][CH2:42][C:43](=[O:45])[CH3:44])=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[CH3:27])=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 11307668HCID 11307668, compound

Product 1

HCID 86597671HCID 86597671, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 457 mg (3.60 mmol) oxalyl chloride in 17 ml dichloromethane was added dropwise during 5 minutes at −75° C. a solution of 562 mg (7.20 mmol) dimethyl sulfoxide in 5 ml dichloromethane. After stirring for 5 minutes a solution of 1.72 g (3.00 mmol) (RS)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-hydroxy-propylamino)-pyridin-3-yl]-N-methyl-isobutyramide in 5 ml dichloromethane was added dropwise at −65° C. Stirring was continued at −70° C. for 1 h, followed by addition of 2.6 ml (15 mmol) ethyldiisopropylamine. After stirring at room temperature for 3 h the reaction mixture was diluted with 20 ml dichloromethane and washed with 20 ml water, 20 ml 1 N hydrochloric acid solution and 20 ml saturated sodium carbonate solution. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 1.45 g (85%) of the title compound as a white foam.

Workup

  1. additionwas added dropwise at −65° C
  2. stirringAfter stirring at room temperature for 3 h the reaction mixture
  3. washwashed with 20 ml water, 20 ml 1 N hydrochloric acid solution and 20 ml saturated sodium carbonate solution
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-09f3b72de36c45d0972206e1bb8a0dfc
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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