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Water → N-(5-Benzyl-thiophen-2-ylmethyl)-6-methylamino-nicotinamide

HRID 2080222
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인쇄 미리보기

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HRID 2080222 반응식
[CH2:1]([C:8]1[S:12][C:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23]OC)=[N:18][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(OCC)(=O)C>CS(C)=O.CO>[CH2:1]([C:8]1[S:12][C:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[N:18][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl Acetate2회HCID 4311764Sodium borohydrideHCID 23130744N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide

생성물 1

HCID 23130402N-(5-Benzyl-thiophen-2-ylmethyl)-6-methylamino-nicotinamide수율 38.8%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 887Methanol용매

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온도
140 °C

실험 절차

To a solution of N-(5-benzyl-thiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide described in Example A-159 (183 mg, 0.52 mmol) in dimethylsulfoxide (3 mL) was added sodium borohydride (120 mg, 3.12 mmol), and the solution was stirred at 140° C. for 5 hours. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed with water twice. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=10:1), and the title compound (68 mg, 0.20 mmol, 38.8%) was obtained as a green solid.

후처리

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. additionSilica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo for adsorption, purification

출처 및 근거

ORD 기록
ord-ff774ce0e8144e0980ad673ecd78825d
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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