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

HRID 2276889ノート

反応式

HRID 2276889 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.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(N(CC)CC)C>O1CCCC1>[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][S:38]([CH3:37])(=[O:40])=[O:39])([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

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 573428821-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-amine

生成物 1

HCID 57342884N-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-yl)methanesulfonamide収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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, 36.5 mg, 0.068 mmol), methanesulfonyl chloride (2 eq, 0.01 mL, 0.135 mmol), and triethylamine (3 eq, 0.03 mL, 0.203 mmol) was stirred in tetrahydrofuran 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)methanesulfonamide (27 mg, 65%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 2.18 (d, J=4.52 Hz, 6H) 2.21-2.37 (m, 2H) 2.39-2.61 (m, 2H) 3.65 (t, J=10.69 Hz, 1H) 3.86 (t, J=10.93 Hz, 1H) 4.07-4.20 (m, 2H) 4.29 (d, J=13.75 Hz, 1H) 5.30 (s, 1H) 7.03-7.11 (m, 2H) 7.15-7.21 (m, 1H) 7.21-7.38 (m, 4H) 7.38-7.47 (m, 2H) 7.47-7.55 (m, 2H).

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-06747030e8a541419bec028443b2cb56
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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