N-(2-aminoethyl)acetamide → N-(2-(6-chloro-3-nitropyridin-2-ylamino)ethyl)acetamide

HRID 1684990

反応式

HRID 1684990 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(N(CC)C(C)C)(C)C.[C:21]([NH:24][CH2:25][CH2:26][NH2:27])(=[O:23])[CH3:22]>C1COCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:27][CH2:26][CH2:25][NH:24][C:21](=[O:23])[CH3:22])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 66082N-(2-aminoethyl)acetamideHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridine

生成物 1

HCID 43553026N-(2-(6-chloro-3-nitropyridin-2-ylamino)ethyl)acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3.0 g (15.5 mmol) 2,6-dichloro-3-nitropyridine in 50 mL of THF at −78° C. under Ar atmosphere was added 2.7 mL (15.5 mmol) of N,N-diisopropylethyl amine followed by 1.6 mL (15.5 mmol) of N-acetylethylenediamine. The mixture was stirred at −78° C. for 30 min, allowed to warm to room temperature, and stirred for 72 hours. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with MeOH/dichloromethane gradient (1→10%) to provide N-(2-(6-chloro-3-nitropyridin-2-ylamino)ethyl)acetamide as pale yellow solid.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 72 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluting with MeOH/dichloromethane gradient (1→10%)

出典と根拠

ORDレコード
ord-2f8a89f695274403ad0ae4919860c78c
出典データセット
uspto-grants-2012_04
特許番号
US08148376B2

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