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

HRID 2080222
ノート
印刷プレビュー

反応式

HRID 2080222 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl Acetate2 回HCID 4311764Sodium borohydrideHCID 23130744N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide

生成物 1

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

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 887Methanol溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ff774ce0e8144e0980ad673ecd78825d
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932272B2

反応ノート

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