Dichloromethane → HCID 23114888, compound

HRID 2080466Notes

Reaction equation

HRID 2080466 reaction equation
C(Cl)Cl.Cl.Cl.[Cl:6][C:7]1[C:8]([CH:18]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:9][C:10]([NH:13][CH2:14][CH2:15][CH2:16][NH2:17])=[N:11][CH:12]=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>CCOCC>[Cl:6][C:7]1[C:8]([CH:18]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)(=[O:28])=[O:29])[C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:9][C:10]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][S:45]([CH3:44])(=[O:47])=[O:46])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23114814HCID 23114814, compound

Product 1

HCID 23114888HCID 23114888, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a methylene chloride solution (5.0 ml) of the N-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl]propane-1,3-diamine dihydrochloride (60 mg, 0.107 mmol) obtained in Example 173 were added triethylamine (70 μl, 0.05 mmol) and methanesulfonyl chloride (10 μl, 0.13 mmol). The resulting mixture was stirred for 20 minutes. To the reaction mixture was added ether (50 ml). The resulting mixture was washed with water and brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the title compound (60 mg, 99%). The resulting compound was crystallized in ethanol to afford a white solid (46 mg).

Workup

  1. washThe resulting mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3782883a1e7043c185b1bb112feea24d
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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