Pyridine → HCID 58734245, compound

HRID 2080524Notes

Reaction equation

HRID 2080524 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1.N1C=CC=CC=1.Cl[S:38]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])(=[O:40])=[O:39]>CCCCCC.C(OCC)(=O)C>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][S:38]([NH:11][C:8]1[CH:7]=[C:6]([CH:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[C:5]([Cl:4])=[CH:10][N:9]=1)(=[O:40])=[O:39])[CH3:46]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 6344Dichloromethane3×HCID 12225100Ethyl (chlorosulfonyl)acetate2×HCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

Product 1

HCID 58734245HCID 58734245, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (10 ml) solution of the [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine (331 mg, 0.771 mmol) obtained in Example 196 and pyridine (94 μl, 1.16 mmol) was added a methylene chloride (2 ml) solution of ethyl chlorosulfonylacetate (216 mg, 1.16 mmol) at 0° C. After the resulting mixture was stirred at room temperature for 12 hours, pyridine (94 up, 1.16 mmol) and a methylene chloride (2 ml) solution of ethyl chlorosulfonylacetate (216 mg, 1.16 mmol) were added sequentially at 0° C. The resulting mixture was stirred at room temperature for 9 hours and then, the reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture 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 (=3:1) eluate was concentrated under reduced pressure to give the title compound (239 mg, 0.412 mmol, 53%) as a white solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 9 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customTo the residue thus obtained
  4. washThe resulting mixture 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 (=3:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52f9bad9d11948c28528bec9d9323d2a
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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