Acetonitrile → HCID 23114593, compound

HRID 2080520Notes

Reaction equation

HRID 2080520 reaction equation
[C:1](#N)[CH3:2].[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.Cl.CN1[CH2:38][CH2:37][N:36]([S:39](Cl)(=[O:41])=[O:40])[CH2:35][CH2:34]1.C(N(CC)CC)C>CO.O>[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]([NH:11][S:39]([N:36]2[CH2:37][CH2:38][CH:1]([CH3:2])[CH2:34][CH2:35]2)(=[O:41])=[O:40])=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471Triethylamine2×HCID 187987054-Methylpiperazine-1-sulfonyl chloride--hydrogen chloride (1/1)2×HCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

Product 1

HCID 23114593HCID 23114593, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An acetonitrile (5 ml) solution of the [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine (101 mg, 0.235 mmol) obtained in Example 196, 4-methylpiperazine-1-sulfonyl chloride hydrochloride (126 mg, 0.534 mmol) and triethylamine (150 μl, 1.07 mmol) was heated under reflux for 23 hours. To the reaction mixture were added 4-methylpiperazine-1-sulfonyl chloride hydrochloride (126 mg, 0.534 mmol) and triethylamine (150 μl, 1.07 mmol). The resulting mixture was heated under reflux for 22 hours. The reaction mixture was returned to room temperature and then, concentrated under reduced pressure. To the residue thus obtained was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with 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 methanol:methylene chloride (=1:20) eluate was concentrated under reduced pressure to give the title compound (34 mg, 0.057 mmol, 16%) as a pale yellow solid.

Workup

  1. temperatureunder reflux for 23 hours
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 22 hours
  4. customwas returned to room temperature
  5. concentrationconcentrated under reduced pressure
  6. customTo the residue thus obtained
  7. extractionthe resulting mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customThe residue thus obtained
  13. concentrationmethylene chloride (=1:20) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dbc4dd5cd4374824a2e8a008e595f4d9
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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