Water → N-(4-Chlorobenzyl)-2-(4-morpholinylmethyl)-4-oxo-7-(tetrahydro-2-furanylmethyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 1978974ノート

反応式

HRID 1978974 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:26])=[C:12]3[CH:18]=[C:17]([CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[CH:36]1[O:40][CH2:39][CH2:38][CH2:37]1.O>CN(C=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[CH:18]=[C:17]([CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[S:16][C:13]=3[N:14]([CH2:35][CH:36]3[CH2:37][CH2:38][CH2:39][O:40]3)[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 178522939HCID 178522939、化合物

生成物 1

HCID 9806060N-(4-Chlorobenzyl)-2-(4-morpholinylmethyl)-4-oxo-7-(tetrahydro-2-furanylmethyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide収率 3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

N-(4-Chlorobenzyl)-4-hydroxy-2-(4-morpholinylmethyl)thieno[2,3-b]pyridine-5-carboxamide (418 mg) from Example No. 41 and potassium carbonate (152 mg) are suspended in DMF (10 mL) and to the mixture is added tetrahydrofurfurylbromide (125 μL). The reaction mixture is heated to 60° C. for 4 h and then allowed to stand at room temperature for 18 h. The reaction mixture is poured into water (25 mL) and extracted with EtOAc (3×25 mL). The organic layer is dried (Na2SO4) and concentrated. The resulting crude solid is purified by recrystallization from ethanol to afford 15 mg (3%) of the title compound as a white solid.

後処理

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resulting crude solid is purified by recrystallization from ethanol

出典と根拠

ORDレコード
ord-fd18821554294c8cb30823748b9971dc
出典データセット
uspto-grants-2001_05
特許番号
US06239142B1

反応ノート

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