Hydrochloric Acid → 3-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine

HRID 1930331ノート

反応式

HRID 1930331 の反応式
Cl.[N:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][NH2:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19].Cl>CCO>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]=[CH:3][CH:4]=[CH:5]3)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 534086886-Hydrazinylquinoline hydrochloride

生成物 1

HCID 588517633-(tert-Butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-amine収率 51.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-(quinolin-6-yl)hydrazine hydrochloride (4.0 g, 20.5 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (3.6 g, 30 mol) in EtOH (50 mL) and cone. HCl (5 mL) was heated at reflux overnight. After removal of the solvent, the residue was purified by column chromatography to yield 3-t-butyl-1-(quinolin-6-yl)-1H-pyrazol-5-amine (2.8 g, 51% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.84 (d, J=4.2 Hz, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.09 (s, 1H), 8.04 (s, 2H), 7.52 (m, 1H), 5.46 (s, 1H), 5.40 (brs, 2H), 1.29 (s, 9H). MS (ESI) m/z (M+H+): 267.2.

後処理

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

出典と根拠

ORDレコード
ord-2b6aa2da08e04651885f16cb9bdb7fce
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

読み込み中…