Potassium Carbonate → 2-(2-(3-Tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162782ノート

反応式

HRID 1162782 の反応式
Br[CH2:2][C:3]([NH:5][C:6]1[S:10][C:9]2[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[C:7]=1[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:4].[C:21]([C:25]1[C:29]([CH:30]=[O:31])=[CH:28][NH:27][N:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:21]([C:25]1[C:29]([CH:30]=[O:31])=[CH:28][N:27]([CH2:2][C:3]([NH:5][C:6]2[S:10][C:9]3[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=3[C:7]=2[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:4])[N:26]=1)([CH3:24])([CH3:22])[CH3:23]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 595205252-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 178441973HCID 178441973、化合物

生成物 1

HCID 595205022-(2-(3-Tert-butyl-4-formyl-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

2-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1.66 g, 4.60 mmol), 3-tert-butyl-1H-pyrazole-4-carbaldehyde (1.75 g, 11.49 mmol) and potassium carbonate (2.54 g, 18.38 mmol) were mixed with DMF (20 mL) and heated at 70° C. for 2 h. On cooling, the reaction was partitioned between EtOAc and water. The organics were washed with brine, dried over MgSO4 and concentrated directly onto silica for chromatographic purification (0-100% EtOAc/heptane). Concentration in vacuo yielded a white solid (1.64 g, 3.79 mmol, 83%).

後処理

  1. temperatureOn cooling
  2. customthe reaction was partitioned between EtOAc and water
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated directly onto silica for chromatographic purification (0-100% EtOAc/heptane)
  6. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-4a9e4b1801654059b23853ffaf1b1a14
出典データセット
uspto-grants-2010_10
特許番号
US07820707B2

反応ノート

読み込み中…