Dichloromethane → HCID 23114882, compound

HRID 2080406Notes

Reaction equation

HRID 2080406 reaction equation
ClCCl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:15]2[N:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.CN1CCOCC1.Cl[C:39](=[O:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CCCCCC.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:15]2[N:20]=[CH:19][C:18]([CH2:21][NH:22][C:39](=[O:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 20884Ethoxalyl chlorideHCID 23114559[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine

Product 1

HCID 23114882HCID 23114882, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a dichloromethane (4 ml) solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine (30 mg, 0.0734 mmol) obtained in Example 63 were added N-methylmorpholine (10 μl, 0.0881 mmol) and ethyl chloroglyoxylate (9 μl, 0.0807 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to give the title compound (28 mg, 0.0550 mmol, 76%) as a white powder.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:2 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee37076f0cb94a1e8384bbd78c80b6e4
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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