Cesium carbonate → N-(cyanomethyl)-4-methyl-2-[(4-{[4-(methylsulfonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]pentanamide

HRID 1180383ノート

反応式

HRID 1180383 の反応式
[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.ClCCl>[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:25][CH2:26]2)=[O:20])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 85089179N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide

生成物 1

HCID 86605380N-(cyanomethyl)-4-methyl-2-[(4-{[4-(methylsulfonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]pentanamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide from example 17, step 7 (102 mg, 0.23 mmol) in DMF (1 mL), was added methyl sulfonyl chloride (27 μL, 0.35 mmol) and cesium carbonate (91 mg, 0.28 mmol). The mixture was aged for 2 hours under nitrogen atmosphere and was diluted with dichloromethane. The resulting mixture was filtered over celite and concentrated under reduced pressure. The crude residue was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane to afford the title compound.

後処理

  1. filtrationThe resulting mixture was filtered over celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane

出典と根拠

ORDレコード
ord-e3d7f9a26582487896f61746f50fa1ff
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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