Water → 2-Methylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080212ノート

反応式

HRID 2080212 の反応式
C(O[CH2:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9])C.[BH4-].[Na+].O>CS(C)=O>[CH3:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9]

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydride2 回HCID 231304322-(Ethoxymethyl-amino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

生成物 1

HCID 231306962-Methylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide収率 67%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-(ethoxymethyl-amino)-N-(5-phenoxy-thiophene-2-ylmethyl)-nicotinamide described in Preparation Example A+-6 (148 mg, 0.385 mmol) in dimethylsulfoxide (3 mL) was added sodium borohydride (44 mg, 1.15 mmol), and the solution was stirred for 30 minutes at 100° C., followed by stirring for 20 minutes at 110° C. Furthermore, sodium borohydride (35 mg, 0.925 mmol) was added thereto, followed by stirring for 20 minutes at 110° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate, the organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (86 mg, 0.26 mmol, 67%) was obtained.

後処理

  1. stirringby stirring for 20 minutes at 110° C
  2. stirringby stirring for 20 minutes at 110° C
  3. extractionwas then extracted with ethyl acetate
  4. washthe organic layer was sequentially washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-678f674f3e75494cb9068c34d2c9f122
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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