Diisopropylethylamine → Ethyl [4-({butyl[6-(4-chlorophenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269657ノート

反応式

HRID 1269657 の反応式
Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:24]([NH:28][CH2:29][C:30]1[CH:42]=[CH:41][C:33]([O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:32]([CH3:43])[CH:31]=1)[CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:24]([N:28]([CH2:29][C:30]1[CH:42]=[CH:41][C:33]([O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:32]([CH3:43])[CH:31]=1)[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:3]=1)[CH2:25][CH2:26][CH3:27]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 184483222-Bromo-6-(4-chlorophenyl)pyrazineHCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

生成物 1

HCID 58622900Ethyl [4-({butyl[6-(4-chlorophenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate収率 16.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-bromo-6-(4-chlorophenyl)pyrazine (0.27 g, 1 mmol), N,N-diisopropylethylamine (0.18 mL, 1 mmol) and ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (0.42 g, 1.5 mmol) was heated at 100° C. in a sealed reactivial for 18 h. The reaction mixture was then allowed to come to room temperature and the residue dissolved in CH2Cl2 (50 mL), the organic extract was washed water (15 mL) and passed through a hydrophobic frit before concentrating in vacuo. Purification by Biotage™ chromatography (Si, 40 g) eluting 1:9–1:1.5 EtOAc:cyclohexane afforded the title compound as a pale yellow oil 78 mg.

後処理

  1. customto come to room temperature
  2. extractionthe organic extract
  3. washwas washed water (15 mL)
  4. concentrationbefore concentrating in vacuo
  5. customPurification by Biotage™ chromatography (Si, 40 g)
  6. washeluting 1:9–1:1.5 EtOAc

出典と根拠

ORDレコード
ord-c17837fa72f8446c9f6066e0af793a82
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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