5-Amino-2-isobutoxybenzonitrile → N-(3-Cyano-4-isobutoxyphenyl)-1,5-dimethylpyrazole-4-carboxamide

HRID 1744551Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[CH:4]=[N:3]1.ON1C2C=CC=CC=2N=N1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[C:26]([CH:29]=1)[C:27]#[N:28]>C(O)C>[C:27]([C:26]1[CH:29]=[C:22]([NH:21][C:8]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:10])[CH:23]=[CH:24][C:25]=1[O:30][CH2:31][CH:32]([CH3:33])[CH3:34])#[N:28]

Participants

Conditions

Temperature: 78 °C

Procedure

1-Hydroxybenzotriazole 1,5-dimethylpyrazole-4-carboxylate (2 g) and 5-amino-2-isobutoxybenzonitrile (1.9 g) were added to ethanol (25 ml) and the mixture was stirred at 78° C. for 3 h. After evaporation of the solvent, the residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=50:1) to give the title compound (0.8 g), melting point: 160–162° C.

Workup

customAfter evaporation of the solvent
customthe residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=50:1)

Sources & evidence

ORD record: ord-846c6aa5067241aa9992da7668f6cc3d
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015218B1

Reaction notes

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