Triethylamine → 5-amino-1-isopropyl-3-(3-nitrophenyl)-1H-pyrazole-4-carbonitrile

HRID 530969

反応式

HRID 530969 の反応式
CO[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[C:4]([C:7]#[N:8])[C:5]#[N:6].Cl.[CH:19]([NH:22][NH2:23])([CH3:21])[CH3:20].C(N(CC)CC)C>C(O)C>[NH2:6][C:5]1[N:22]([CH:19]([CH3:21])[CH3:20])[N:23]=[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:4]=1[C:7]#[N:8]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 895868902-(Methoxy(3-nitrophenyl)methylene)malononitrile

生成物 1

HCID 895865895-amino-1-isopropyl-3-(3-nitrophenyl)-1H-pyrazole-4-carbonitrile収率 79%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Compound 25 (5 g, 21.8 mmol), isopropylhydrazine hydrochloride (2.41 g, 21.8 mmol) (purchased from Ryan Scientific) and triethylamine (6.40 mL, 46.0 mmol) were allowed to react in ethanol (145 mL) at room temperature for 1 hr. After concentrating the reaction mixture, it was purified by silica chromatography using a chloroform/methanol solvent system (methanol gradient increased with time from 0-10%). The relevant fractions were concentrated in vacuo to yield a yellow powder (4.65 g, 79% yield): 1H NMR (400 MHz, DMSO) δ 8.59 (s, 1H), 8.24 (m, 2H), 7.78 (t, J=8.2, 1H), 6.82 (br, 2H), 4.53 (hept, J =6.5, 1H), 1.36 (d, J=6.5, 6H). 13C NMR (100 MHz, DMSO) δ 153.04, 148.76, 146.98, 133.97, 132.22, 131.19, 123.80, 120.37, 116.28, 70.74, 48.64, 22.02; [M+H]+ calculated for C13H11N5O2 272.1, found 272.3.

後処理

  1. concentrationAfter concentrating the reaction mixture, it
  2. customwas purified by silica chromatography
  3. temperaturea chloroform/methanol solvent system (methanol gradient increased with time from 0-10%)
  4. concentrationThe relevant fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-29edc366a9494e4a814ef8ba2c046876
出典データセット
uspto-grants-2016_05
特許番号
US09353116B2

関連ノート

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