1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 83655

反応式

HRID 83655 の反応式
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20](O)=[O:21])[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.C(Cl)CCl.[CH:29]1[CH:30]=[CH:31][C:32]2N(O)N=[N:35][C:33]=2C=1.[N:39]1C=CC=[CH:41][C:40]=1CCN>CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]([NH:39][CH2:40][CH2:41][C:31]3[CH:30]=[CH:29][N:35]=[CH:33][CH:32]=3)=[O:21])[CH2:18][CH2:19]2)=[O:13])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 683802051-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid

生成物 1

HCID 665715681-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

The following was added sequentially to DCM: 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid (600 mg, 1.73 mmol), TEA (0.725 mL, 5.19 mmol), EDC (365 mg, 1.903 mmol), and HOBt (291 mqg, 1.903 mmol). This was allowed to stir at rt for 30 min, at which time pyridylethylamine (0.227 mL, 1.903 mmol) was added. Stirring continued for 18 h. At this time, the DCM and TEA were stripped off, and the residue was taken up in EtOAc and washed with 10% aqueous sodium carbonate (3×). The organic phase was collected, dried over magnesium sulfate, and concentrated in vacuo. The resulting solid/oil mixture was recrystallized from EtOAc to afford the title compound as small, white crystals. (Yield: 586 mg, 1.29 mmol, 75%) 1H NMR (400 MHz, CDCl3) 8.50, 7.21, 7.09, 7.02, 6.78, 6.30, 6.11, 5.55-5.42, 5.25, 4.32, 3.52, 2.87-2.71, 2.28-2.10, 1.72-1.65, 1.42-1.25

後処理

  1. additionwas added
  2. washwashed with 10% aqueous sodium carbonate (3×)
  3. customThe organic phase was collected
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid/oil mixture was recrystallized from EtOAc

出典と根拠

ORDレコード
ord-5d66f650c11140e29a9232faab160fdb
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

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