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

HRID 2276888ノート

反応式

HRID 2276888 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0791e57bceab4f2e8e5ed938ce694a7d
出典データセット
uspto-grants-2015_09
特許番号
US09133128B2

反応ノート

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