Diisopropylethylamine → N-(4-chlorobenzyl)-2-{[{2-hydroxy-2-[4-(2-hydroxyethoxy)phenyl]ethyl}(methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23680노트

반응식

HRID 23680 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[OH:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]([OH:40])[CH2:37][NH:38][CH3:39])=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:38]([CH2:37][CH:36]([OH:40])[C:33]4[CH:34]=[CH:35][C:30]([O:29][CH2:28][CH2:27][OH:26])=[CH:31][CH:32]=4)[CH3:39])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 101490921-[4-(2-Hydroxyethoxy)phenyl]-2-(methylamino)ethanolHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

생성물 1

HCID 10128996N-(4-chlorobenzyl)-2-{[{2-hydroxy-2-[4-(2-hydroxyethoxy)phenyl]ethyl}(methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide수율 57.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), 1-[4-(2-hydroxyethoxy)phenyl]-2-(methylamino)ethanol (Preparation 83) (70 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 4 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (5 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (82 mg) as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
  3. waitleft
  4. waitstanding overnight at room temp
  5. filtrationThe mixture was filtered
  6. washthe collected solid was washed with water
  7. customdried in vacuo
  8. customleaving a white solid
  9. customRecrystallization from acetonitrile (5 mL
  10. dissolutiondissolved
  11. temperaturewith warming
  12. temperaturecooled to 0° C. overnight)

출처 및 근거

ORD 기록
ord-71aba01caf8c41adaa91fb7f93fa78db
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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