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Acetyl chloride → HCID 23028618, compound

HRID 748846
Notes
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Reaction equation

HRID 748846 reaction equation
CN1CCOCC1.C(Cl)(=O)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[C:23]2N=CC(CN)=C[CH:24]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Si:39]([O:46][CH2:47][CH2:48]C(C)C(C1C=C(F)C=CC=1F)S(C1C=CC(Cl)=CC=1)(=O)=O)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]>ClCCl.C(OCC)(=O)C.O>[Si:39]([O:46][CH:47]([CH3:48])[CH2:24][CH2:23][CH:22]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[F:38])[S:19]([C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=1)(=[O:21])=[O:20])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 23114559[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamineHCID 59750761HCID 59750761, compound

Product 1

HCID 23028618HCID 23028618, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, N-methylmorpholine (26 μl, 0.234 mmol) and acetyl chloride (16 μl, 0.234 mmol) were added to a solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine (40 ing, 0.0978 mmol), which had been obtained in Example 351, in dichloromethane (3 ml). The resulting mixture was stirred at room temperature for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column. A fraction obtained from the elution portion with hexane:ethyl acetate=2:3 was concentrated under reduced pressure, whereby the title compound A (low polarity compound) (15 mg, 0.0304 mmol, 40%) was obtained as a white powder and the title compound B (high polarity compound) (12 mg, 0.0266 mmol, 27%) was obtained as a white powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customA fraction obtained from the elution portion with hexane
  6. customwas obtained as a white powder

Sources & evidence

ORD record
ord-faaf6c425689494294b60d748aa51747
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes