Dimethylformamide → 2-chloro-5,6-dimethyl-3-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridin-4-amine

HRID 1008012ノート

反応式

HRID 1008012 の反応式
CN(C)C=O.[Cl:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11](Cl)[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH2:31])[CH:20]=1>C(N(CC)CC)C>[Cl:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([NH:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineHCID 219130212-(3-Pyridin-3-ylpropoxy)ethanamine

生成物 1

HCID 219140062-chloro-5,6-dimethyl-3-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridin-4-amine

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
45 °C

実験手順

Anhydrous N,N-dimethylformamide (200 ml), anhydrous triethylamine (12.1 ml), and 2,4-dichloro-5,6-dimethyl-3-nitropyridine (16.05 g) were combined and 2-(3-pyridin-3-ylpropoxy)ethylamine (14.4 g) was then added with stirring. The pale yellow reaction mixture was heated to 45° C. under a nitrogen atmosphere for 1 hour. HPLC analysis indicated that the reaction was sufficiently complete to proceed. The reaction mixture was allowed to cool and the solvent was removed under reduced pressure. The resulting oil was dissolved in ethyl acetate and washed twice: once with a saturated aqueous solution of ammonium chloride and once with water. The organic layer was then extracted 3 times with brine, dried with magnesium sulfate, and concentrated under reduced pressure. The product was passed through a silica gel column using 90/10 ethyl acetate/hexane as the eluant. The resulting oil was dried under vacuum at 60° C. for 2 hours. NMR analysis indicated sufficient purity for use of the product in the next step.

後処理

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. washwashed twice
  5. extractionThe organic layer was then extracted 3 times with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was dried under vacuum at 60° C. for 2 hours

出典と根拠

ORDレコード
ord-a1a7c3b10ebc4d4fbdc2126ddfab01a2
出典データセット
uspto-grants-2004_09
特許番号
US06797718B2

反応ノート

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