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

HRID 1269637노트

반응식

HRID 1269637 반응식
Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[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]([CH3:14])=[CH:10][CH:9]=2)[N:3]=1)[CH2:25][CH2:26][CH3:27]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 184483232-Bromo-6-(4-methylphenyl)pyrazineHCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

생성물 1

HCID 58622854Ethyl [4-({butyl[6-(4-methylphenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate수율 8.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

A mixture of 2-bromo-6-(4-methylphenyl)pyrazine (0.25 g, 1 mmol), N,N-diisopropylethylamine (0.35 mL, 2 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 (30 mL), the organic extract was washed water (15 mL) and passed through a hydrophobic frit before concentrating in vacuo. Purification by Biotage™ chromatography (Silica, 40 g) eluting 1:19–1:4 EtOAc:cyclohexane afforded the title compound as a pale yellow oil (37 mg).

후처리

  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 (Silica, 40 g)
  6. washeluting 1:19–1:4 EtOAc

출처 및 근거

ORD 기록
ord-e764d4364f0b4d809332dfed447a9042
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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