Methyl iodide → N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

HRID 1978957

反応式

HRID 1978957 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:21])=[C:12]3[CH:18]=[C:17]([CH2:19][OH:20])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:21])[C:12]3[CH:18]=[C:17]([CH2:19][OH:20])[S:16][C:13]=3[N:14]([CH3:24])[CH:15]=2)=[O:9])=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522940HCID 178522940、化合物

生成物 1

HCID 6482399N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(hydroxymethyl)thieno[2,3-b]pyridine-5-carboxamide (0.955 g) from Example No. 34 in DMF (20 mL) is added potassium carbonate (0.567 g) followed by iodomethane (0.20 mL). The reaction is stirred at rt for 1 h. The reaction mixture is partitioned between water (50 mL) and CH2Cl2 (100 mL). The aqueous layer is extracted with CH2Cl2 (100 mL). The organic layer is removed in vacuo and insoluble material in the aqueous layer is filtered off. The resulting solid is recrystallized from ethanol to yield 0.825 g (83%) of the title compound as a white, crystalline solid.

後処理

  1. customThe reaction mixture is partitioned between water (50 mL) and CH2Cl2 (100 mL)
  2. extractionThe aqueous layer is extracted with CH2Cl2 (100 mL)
  3. customThe organic layer is removed in vacuo and insoluble material in the aqueous layer
  4. filtrationis filtered off
  5. customThe resulting solid is recrystallized from ethanol

出典と根拠

ORDレコード
ord-00549256b70545cc891710bcd6b6f8b0
出典データセット
uspto-grants-2001_05
特許番号
US06239142B1

関連ノート

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