Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate

HRID 1696485노트

반응식

HRID 1696485 반응식
Cl.[CH2:2]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([NH:17][NH2:18])[CH:8]=1)=[O:6])[CH3:3].[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24]>CCO.Cl>[NH2:24][C:23]1[N:17]([C:9]2[CH:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:18]=[C:21]([C:20]([CH3:27])([CH3:26])[CH3:19])[CH:22]=1

참가 물질

5

반응물 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67271149Ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride

생성물 1

HCID 58851682ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate수율 95.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

A mixture of 3-hydrazinonaphthalene-1-carboxylic acid ethyl ester hydrochloride (1.5 g, 5.6 mmol) and 4,4-dimethyl-3-oxopentanenitrile (875 mg, 7.0 mmol) in EtOH (50 mL) and conc. HCl (5 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to yield ethyl 3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1-naphthoate (1.8 g, 95% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.74 (d, J=6.3 Hz, 1H), 8.47 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=6.0 Hz, 1H), 7.76 (t, J=5.7 Hz, 1H), 7.71 (t, J=5.7 Hz, 1H), 5.68 (s, 1H), 4.44 (q, J=5.4 Hz, 2H), 1.37 (t, J=5.4 Hz, 3H), 1.30 (s, 9H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-cb1abdcf015d40cf81e2b326efb74600
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163756B2

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