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

HRID 530969

Reaktionsgleichung

Reaktionsgleichung von HRID 530969
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-29edc366a9494e4a814ef8ba2c046876
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353116B2

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