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Sodium Hydroxide → HCID 22574302, 화합물

HRID 23644
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HRID 23644 반응식
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:40])[C:12]3[S:19][C:18]([CH2:20][N:21]([CH2:23][CH:24]([OH:31])[C:25]4[CH:30]=[N:29][CH:28]=[CH:27][N:26]=4)[CH3:22])=[C:17]([CH2:32][O:33]CC[Si](C)(C)C)[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:40])[C:12]3[S:19][C:18]([CH2:20][N:21]([CH2:23][CH:24]([OH:31])[C:25]4[CH:30]=[N:29][CH:28]=[CH:27][N:26]=4)[CH3:22])=[C:17]([CH2:32][OH:33])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22574381N-(4-chlorobenzyl)-2-{[(2-hydroxy-2-pyrazin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

생성물 1

HCID 22574302HCID 22574302, 화합물수율 94.2%

시약·촉매·용매 3

HCID 6212
Chloroform
용매
HCID 6344Dichloromethane용매
HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 144 mg of N-(4-chlorobenzyl)-2-{[(2-hydroxy-2-pyrazin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 3 mL of 75% TFA in CH2Cl2 is stirred at room temperature for 3 h, then diluted with CHCl3 and added to stirred aq. NaHCO3. The aqueous phase is adjusted to pH 10-11 with added NaOH, then extracted with 6 portions of CHCl3. The combined organic phase is dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica gel (compound pre-loaded onto silica gel using CHCl3-MeOH) using 5-8% MeOH in CH2Cl2 provides 114 mg of the title compound as a white solid. Trituration with boiling acetonitrile affords white solid.

후처리

  1. additionadded
  2. extractionextracted with 6 portions of CHCl3
  3. dry with materialThe combined organic phase is dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d041c45dc7384a0ba93c0c0652890974
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06852731B2

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