Acetyl chloride → HCID 22037230, compound

HRID 861094Notes

Reaction equation

HRID 861094 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:4][CH2:3]1.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:26]([N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:6][CH2:7]1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 22037252HCID 22037252, compound

Product 1

HCID 22037230HCID 22037230, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (1 g, 2.4 mmol) in 24 mL of CH2Cl2 was added 4-dimethylamino pyridine (0.88 g, 7.2 mmol) and acetyl chloride (0.21 g, 2.6 mmol). The solution was stirred for 3 h and the solvent was removed under reduced pressure. The residue was treated with saturated NH4OH (20 mL) and the suspension was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with brine (1×50 mL), dried over MgSo4, filtered and concentrated to leave a solid. The solid was triturated with ether and was filtered to leave the title compound: MS (M+H): 381 (base peak).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was treated with saturated NH4OH (20 mL)
  3. extractionthe suspension was extracted with ethyl acetate (3×30 mL)
  4. washThe combined extracts were washed with brine (1×50 mL)
  5. customdried over MgSo4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto leave a solid
  9. customThe solid was triturated with ether
  10. filtrationwas filtered

Sources & evidence

ORD record
ord-ea90bf4336d349e886bc7942217c0668
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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