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

HRID 530969

Reaction equation

HRID 530969 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-29edc366a9494e4a814ef8ba2c046876
Source dataset
uspto-grants-2016_05
Patent number
US09353116B2

Linked notes

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