Water → 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23623

반응식

HRID 23623 반응식
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:22])=[C:12]3[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:32][C:33]([NH2:35])=[O:34].O>CN(C=O)C>[NH2:35][C:33](=[O:34])[CH2:32][N:14]1[CH:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][CH:23]=2)=[O:9])[C:11](=[O:22])[C:12]2[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]1=2

참가 물질

6

반응물 4

HCID 962WaterHCID 3727Iodoacetamide2회HCID 11430Potassium Carbonate2회HCID 178429625HCID 178429625, 화합물

생성물 1

HCID 225743684-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide수율 56.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A mixture of N-(4-chlorobenzyl)-7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.276 mmol), potassium carbonate (57 mg, 0.41 mmol) and iodoacetamide (255 mg, 1.38 mmol) in DMF (1.5 mL) was stirred at 50° C. for 18 hrs. Additional iodoacetamide (255 mg) and potassium carbonate (57 mg) were added, and the reaction was stirred at the same temperature for another 12 hrs. After cooling, cold water was added, and the resulting ppt was collected by filtration after chilling in an ice bath. The collected crude solid was recrystallized from aq. ethanol to give the title compound (65 mg) as a lt. brown solid.

후처리

  1. stirringthe reaction was stirred at the same temperature for another 12 hrs
  2. temperatureAfter cooling
  3. filtrationthe resulting ppt was collected by filtration
  4. temperatureafter chilling in an ice bath
  5. customThe collected crude solid
  6. customwas recrystallized from aq. ethanol

출처 및 근거

ORD 기록
ord-a2a3ee5c1f5d4061bd2b4e9afb037b1c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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