Dichloromethane → HCID 23114701, compound

HRID 2080489Notes

Reaction equation

HRID 2080489 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])=[CH:7][C:8]([NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:9][CH:10]=1.C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>C(OCC)(=O)C.CCCCCC>[Cl:4][C:5]1[C:6]([CH:20]([S:29]([C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)(=[O:31])=[O:30])[C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])=[CH:7][C:8]([N:11]([S:47]([CH3:46])(=[O:49])=[O:48])[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 23114703HCID 23114703, compound

Product 1

HCID 23114701HCID 23114701, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (5 ml) solution of t-butyl N′-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]hydrazine carboxylate (178 mg, 0.327 mmol) and triethylamine (43 μl, 0.392 mmol) was added methanesulfonyl chloride (30 μl, 0.392 mmol) at 0° C. The resulting mixture was stirred at room temperature for 16 hours. To the reaction mixture were added triethylamine (43 μl, 0.392 mmol) and methanesulfonyl chloride (30 μl, 0.392 mmol). After stirring at room temperature for 3 hours, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was diluted with ethyl acetate. The diluted solution was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine, 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 (=4:1) eluate was concentrated under reduced pressure to give the title compound (174 mg, 0.280 mmol, 85%) as a white solid.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. washThe diluted solution was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate (=4:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-96e4eb5b5e9547428f0a38cef834d906
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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