Dichloromethane → HCID 58734262, compound

HRID 2080490Notes

Reaction equation

HRID 2080490 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:24]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])=[CH:7][C:8]([N:11]([S:20]([CH3:23])(=[O:22])=[O:21])[NH:12]C(OC(C)(C)C)=O)=[N:9][CH:10]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>CCCCCC>[Cl:4][C:5]1[C:6]([CH:24]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)(=[O:34])=[O:35])[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])=[CH:7][C:8]([N:11]([S:20]([CH3:23])(=[O:22])=[O:21])[NH2:12])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 23114701HCID 23114701, compound

Product 1

HCID 58734262HCID 58734262, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a methylene chloride (5 ml) solution of t-butyl N′-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]-N′-methylsulfonylhydrazine carboxylate (167 mg, 0.268 mmol) was added trifluoroacetic acid (2.5 ml). The resulting mixture was stirred at room temperature for 21 hours, followed by concentration under reduced pressure. To the residue thus obtained was added a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with methylene chloride. The organic layer obtained by separation 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 (=2:1) eluate was concentrated under reduced pressure to afford the title compound (91 mg, 0.174 mmol, 65%) as a white solid. The resulting solid was washed with ether and collected by filtration to give the title compound (60 mg) as a white powder.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customTo the residue thus obtained
  3. extractionThe resulting mixture was extracted with methylene chloride
  4. customThe organic layer obtained by separation
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a07ca8d0099b4be4bea0720f7a6a8899
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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