Tetrahydrofuran → HCID 68996099、化合物

HRID 28932ノート

反応式

HRID 28932 の反応式
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[CH3:23][C:24](C)([O-:26])[CH3:25].[K+].O1CC[CH2:31][CH2:30]1.O1CCCC1Br>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][N:5]([CH2:23][CH:24]2[CH2:25][CH2:31][CH2:30][O:26]2)[CH:6]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 130702942-BromotetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178521959HCID 178521959、化合物

生成物 1

HCID 68996099HCID 68996099、化合物収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea (0.28 mmol) in anhydrous N,N-dimethylformamide (6 mL) cooled to 0° C. was added 1.0M potassium tert-butoxide in tetrahydrofuran (1.12 mmol) dropwise. The reaction mixture was stirred for a further 15 minutes in the cold before dropwise addition of tetrahydrofuryl bromide (0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by quenching with saturated aqueous ammonium chloride (1 mL). The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Gilson reverse phase HPLC afforded the title compound (53%). ESMS [M+H]+: 441.4

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. customby quenching with saturated aqueous ammonium chloride (1 mL)
  3. additionThe reaction mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-27222053011f4de199da5d330d6b767a
出典データセット
uspto-grants-2008_09
特許番号
US07419988B2

反応ノート

読み込み中…