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Acetyl chloride → HCID 57940700, compound

HRID 1437308
Notes
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Reaction equation

HRID 1437308 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH3:12][O:13][C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:23][C:22]([C:31]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][NH:34]3)=[O:32])=[N:21]2)=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:12][O:13][C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:23][C:22]([C:31]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][N:34]3[C:8](=[O:10])[CH3:9])=[O:32])=[N:21]2)=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11674985HCID 11674985, compound

Product 1

HCID 57940700HCID 57940700, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344Dichloromethane
Solvent

Procedure

Triethylamine (0.210 mL), acetyl chloride (0.0807 mL) and 4-dimethylaminopyridine (13.5 mg) were added to 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]hexahydropyridazine (0.275 g) obtained in Example 162 in methylene chloride (6.0 mL) at room temperature, followed by stirring for 20 minutes. The mixture was partitioned between water and chloroform. The organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an amorphous product (0.149 g, 59%).

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. filtrationThe mixture was subjected to filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-8a17b77d638f45a3a1b6f6114b955e90
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622471B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes