Sodium Iodide → 3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamide

HRID 1878438ノート

反応式

HRID 1878438 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:16].Cl[CH2:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=1)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]1[CH2:29][CH2:28]1)[CH3:26])=[O:23].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:18][C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=3)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]3[CH2:29][CH2:28]3)[CH3:26])=[O:23])[CH2:14][CH2:15]2)=[O:9])=[CH:4][C:3]=1[F:16]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 63187976(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanoneHCID 66878470HCID 66878470、化合物

生成物 1

HCID 579176753-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamide収率 15.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanone (2.74 mmol, 0.612 g), 3-(chloromethyl)-N-(1-cyano-1-cyclopropylethyl)benzamide (2.74 mmol, 0.72 g), sodium iodide (0.548 mmol, 0.082 g) and potassium carbonate (8.22 mmol, 1.136 g) were combined in acetonitrile (25 mL) and heated to reflux for 2 hours. The reaction was concentrated under reduced pressure and the resulting residue taken up in dichloromethane and washed with water. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane) to afford the title compound (195 mg). MS (ESI) m/z 450.3 [M+H]+

後処理

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-152cba8e56a9490eb5b0a956bdb1b975
出典データセット
uspto-grants-2012_11
特許番号
US08314091B2

反応ノート

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