5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carbonitrile → 5-amino-1-cyclobutyl-1H-pyrazole-4-carbonitrile

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=CC=2OC)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].C1(NN)CCC1>>[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10]2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16]

Participants

Reactant 2

HCID 121505605-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carbonitrile

HCID 18699355Cyclobutylhydrazine

Product 1

HCID 498535445-amino-1-cyclobutyl-1H-pyrazole-4-carbonitrile

Procedure

Following the procedure for the preparation of 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carbonitrile but substituting 1-cyclobutylhydrazine provided the title compound. 400 MHz 1H NMR (CDCl3) δ 7.50 (s, 1H), 4.48-4.40 (m, 1H), 4.23 (m, 2H), 2.70-2.58 (m, 2H), 2.48-2.35 (m, 2H), 1.97-1.79 (m, 2H). MS: (M+H m/z 163.1).

Sources & evidence

ORD record: ord-7959455f01b2429481a07961677de492
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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