Acetyl chloride → HCID 23090451, compound

HRID 1437300Notes

Reaction equation

HRID 1437300 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].Cl.[CH3:13][O:14][C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:24][C:23]([C:32]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[O:33])=[N:22]2)=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:13][O:14][C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:24][C:23]([C:32]([N:34]3[CH2:39][CH2:38][N:37]([C:8](=[O:10])[CH3:9])[CH2:36][CH2:35]3)=[O:33])=[N:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23090518HCID 23090518, compound

Product 1

HCID 23090451HCID 23090451, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., triethylamine (0.205 mL) and acetyl chloride (0.0447 mL) were added to a solution of 4-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]piperazine hydrochloride (0.185 g) obtained in Example 81 in methylene chloride (5.0 mL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between water and chloroform. The aqueous layer was further extracted with chloroform, and the organic layers were combined, followed by washing with saturated brine and drying over sodium sulfate anhydrate. After filtration, 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 (0.147 g, 87%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. extractionThe aqueous layer was further extracted with chloroform
  3. washby washing with saturated brine
  4. dry with materialdrying over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-b7abd60efde64bef83ae946b99076ecb
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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