Acetic Anhydride → HCID 57343392, compound

HRID 2276894Notes

Reaction equation

HRID 2276894 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([CH3:22])=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:18]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[C:38](OC(=O)C)(=O)C>N1C=CC=CC=1>[C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]2[C:21]([CH3:22])=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:18]=2)=[O:16])[CH2:12][CH2:13]1)(=[O:7])[CH3:38]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57343390HCID 57343390, compound

Product 1

HCID 57343392HCID 57343392, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl-4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate (1 eq, 34 mg, 0.073 mmol) was stirred in pyridine (1 mL) and acetic anhydride (1 mL) for 16 h. The reaction was concentrated in vacuo. The crude reaction material was purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure N-(1-acetylpiperidin-4-yl)-5-(4-chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxamide (30 mg, 81%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.28-1.49 (m, 2H) 1.87-2.13 (m, 5H) 2.30 (s, 3H) 2.62-2.82 (m, 1H) 3.05-3.24 (m, 1H) 3.75 (d, J=13.56 Hz, 1H) 3.98-4.25 (m, 1H) 4.49 (d, J=13.37 Hz, 1H) 6.80 (d, J=8.01 Hz, 1H) 6.99 (d, J=8.48 Hz, 2H) 7.13-7.29 (m, 4H) 7.36 (d, J=1.51 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude reaction material
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ac2e0eb090240f69cc74c555022f103
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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