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Acetic Acid → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23636
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인쇄 미리보기

반응식

HRID 23636 반응식
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH:20]=[O:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH2:20][OH:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:29][CH:30]=1
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 22574380N-(4-Chlorobenzyl)-2-formyl-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

생성물 1

HCID 22574407N-(4-Chlorobenzyl)-2-(hydroxymethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide수율 102.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a cold (0° C.), stirred solution of 1.05 g of N-(4-chlorobenzyl)-2-formyl-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 20 mL of CH2Cl2 is added 0.67 mL of acetic acid and 1.5 g of sodium triacetoxyborohydride. The mixture is allowed to warm to room temperature and stirred for 2 h, then partitioned between CH2Cl2 and aqueous NaHCO3. The organic phase is dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 2.5-4% MeOH in CH2Cl2 affords 1.08 g (100%) of the title compound as a yellow crystalline solid. Recrystallization from acetonitrile affords white spars.

후처리

  1. custompartitioned between CH2Cl2 and aqueous NaHCO3
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-65100645ed5f426e93aa131ca3d0aed1
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06852731B2

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