Acetic Anhydride → N-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)acetamide

HRID 2276888Notes

Reaction equation

HRID 2276888 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:23]3[CH2:28][CH2:27][C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([NH2:29])[CH2:25][CH2:24]3)=[O:22])[C:9]=2[CH3:36])=[CH:4][CH:3]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:23]3[CH2:24][CH2:25][C:26]([NH:29][C:37](=[O:39])[CH3:38])([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:27][CH2:28]3)=[O:22])[C:9]=2[CH3:36])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 573428821-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-amine

Product 1

HCID 57342883N-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)acetamideYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-{[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-amine (1 eq, 35.3 mg, 0.066 mmol) was stirred in a mixture of acetic anhydride (2 mL) and pyridine (2 mL) for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure N-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)acetamide (27 mg, 71%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 2.01 (s, 3H) 2.05-2.19 (m, 2H) 2.21 (s, 3H) 2.34 (d, J=14.60 Hz, 1H) 2.66 (d, J=13.85 Hz, 1H) 3.15-3.34 (m, 1H) 3.52 (t, J=11.68 Hz, 1H) 4.26 (d, J=13.75 Hz, 1H) 4.54 (d, J=13.75 Hz, 1H) 6.10 (s, 1H) 7.03-7.11 (m, 2H) 7.14-7.19 (m, 1H) 7.19-7.41 (m, 8H) 7.44 (d, J=2.17 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-0791e57bceab4f2e8e5ed938ce694a7d
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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