Dimethylformamide → N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide

HRID 13485

反応式

HRID 13485 の反応式
FC1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][Si]([N-][Si](C)(C)C)(C)C.[K+].OC1C=[C:25]([C:29]([NH:31][CH3:32])=O)[CH:26]=[CH:27]C=1.[C:33](=[O:36])([O-])[O-].[K+].[K+].[CH3:39][N:40](C)[CH:41]=[O:42]>>[CH3:39][NH:40][C:41]([C:29]1[CH:25]=[C:26]([O:36][C:33]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:8][CH3:12])[CH:7]=2)[CH:27]=[CH:32][N:31]=1)=[O:42]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 753995-Fluoro-2-nitroanilineHCID 3537103-hydroxy-N-methylbenzamideHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 131725842N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide

反応条件

温度
90 °C

実験手順

The mixture containing 5-fluoro-2-nitrophenylamine (1 eq), Potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (3-hydroxyphenyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and stirred at 90° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel gave N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide. It was taken in methanol and hydrogenated with catalytic amount of 10% Pd/C to give {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide. MS: MH+=272.

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification on silica gel

出典と根拠

ORDレコード
ord-6b6dff67f14a4b098baa503d8c3178a8
出典データセット
uspto-grants-2010_06
特許番号
US07728010B2

関連ノート

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