Dichloromethane → HCID 59750817, compound

HRID 748777Notes

Reaction equation

HRID 748777 reaction equation
CN1CCOCC1.[CH3:8][S:9](Cl)(=[O:11])=[O:10].ClCCl.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH:27]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[CH2:28][CH2:29][CH2:30][NH2:31])(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(OCC)(=O)C.CCCCCC.CCCCCC>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([CH:27]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[CH2:28][CH2:29][CH2:30][NH:31][S:9]([CH3:8])(=[O:11])=[O:10])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 79724-Methylmorpholine2×HCID 31297Methanesulfonyl chloride2×HCID 69202069HCID 69202069, compound

Product 1

HCID 59750817HCID 59750817, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under a nitrogen atmosphere, N-methylmorpholine (51.0 μl, 0.465 mmol) and methanesulfonyl chloride (18.8 μl, 0.242 mmol) were added to a dichloromethane solution (4 ml) of the 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)butylamine hydrochloride (80.0 mg, 0.202 mmol) obtained in Example 227. After stirring at room temperature for 15 hours, N-methylmorpholine (156 μl, 1.42 mmol) and methanesulfonyl chloride (10.0 μl, 0.129 mmol) were added. The resulting mixture was stirred at room temperature for 2 hours. After dilution with dichloromethane, the mixture was successively washed with a saturated aqueous solution of ammonium chloride, water, and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (71.5 mg, 0.163 mmol, 81%) was obtained as colorless plate crystals.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. washAfter dilution with dichloromethane, the mixture was successively washed with a saturated aqueous solution of ammonium chloride, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. concentrationethyl acetate=1:1 eluate was concentrated
  7. customThe solid thus obtained

Sources & evidence

ORD record
ord-9c3a35a18cea4f90876480ac8d7a8a9b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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