Dichloromethane → HCID 23114788, compound

HRID 2080504Notes

Reaction equation

HRID 2080504 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.ClCCl.[Cl:16][C:17]1[C:18]([CH:24]([C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])[S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=2)(=[O:27])=[O:26])=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1>CN(C)C1C=CN=CC=1.CCCCCC>[Cl:16][C:17]1[C:18]([CH:24]([C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])[S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=2)(=[O:26])=[O:27])=[CH:19][C:20]([N:23]([S:2]([CH3:1])(=[O:4])=[O:3])[S:2]([CH3:1])(=[O:4])=[O:3])=[N:21][CH:22]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23114597HCID 23114597, compound

Product 1

HCID 23114788HCID 23114788, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, methanesulfonyl chloride (0.034 ml, 0.44 mmol), triethylamine (0.062 ml, 0.44 mmol) and 4-dimethylaminopyridine (4 mg, 0.03 mmol) were added to a dichloromethane (3 ml) solution of [5-chloro-4-[(2,5-difluorophenyl)(3,4-difluorophenylsulfonyl)methyl]pyridin-2-yl]amine (63 mg, 0.15 mmol) at 0° C. The resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (73 mg, 0.12 mmol, 85%) as a white solid.

Workup

  1. washThe reaction mixture was washed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a19adb8b3bdc4aea93700adb1b3e059e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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