Cyclopropylamine → HCID 67432850、化合物

HRID 2036612ノート

反応式

HRID 2036612 の反応式
Br[C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C1COCC1.CCOC(C)=O>[C:7]([NH:6][C:4](=[O:5])[C:3]1[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:2]=1[NH:21][CH:18]1[CH2:20][CH2:19]1)([CH3:10])([CH3:9])[CH3:8]

参加物

5

反応物 2

HCID 69828CyclopropylamineHCID 674309942-bromo-N-tert-butyl-3-nitrobenzamide

生成物 1

HCID 67432850HCID 67432850、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-bromo-N-tert-butyl-3-nitrobenzamide (460 mg, 1.52 mmol) and cyclopropanamine (350 μL, 4.55 mmol) in THF (10 mL) was heated at 60° C. for 18 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAC:DCM (1:1) as eluent to give N-tert-butyl-2-(cyclopropylamino)-3-nitrobenzamide: 1H NMR (400 MHz, CDCl3) δ 8.26 (1H, br), 8.09 (1H, dd, J=8.0, 4.0 Hz), 7.57 (1H, d, J=8.0 Hz), 6.72 (1H, t, J=8.0 Hz), 5.81 (1H, br), 2.98-2.92 (1H, m), 1.49 (9H, s), 0.82-0.76 (2H, m), 0.58-0.52 (2H, m); LC-MS (ESI) m/z 278.2 [M+H]+.

後処理

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel using EtOAC

出典と根拠

ORDレコード
ord-89f11ad4778a46868bbd34d3bcb46ef6
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

反応ノート

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