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

HRID 1978957

반응식

HRID 1978957 반응식
[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

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522940HCID 178522940, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00549256b70545cc891710bcd6b6f8b0
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239142B1

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