Acetic Acid → N-[6-(1-Cyano-4-oxocyclohexyl)pyridin-3-yl]-5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide

HRID 1748639Notes

Reaction equation

[C:1]([C:3]1([C:13]2[N:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)[C:26]=3[CH3:27])=[O:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1)#[N:2].C(O)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:3]1([C:13]2[N:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)[C:26]=3[CH3:27])=[O:21])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide (181 mg) described in Example E3 in a mixed solvent of acetic acid (2 ml), water (0.5 ml) and 1N hydrochloric acid aqueous solution (0.5 ml) was stirred at 100° C. for two hours. After the reaction, a saturated aqueous solution of potassium carbonate was added and extracted with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with a column chromatography to give the titled compound (96 mg).

Workup

customAfter the reaction
extractionextracted with ethyl acetate
dry with materialThe organic solution was dried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified with a column chromatography

Sources & evidence

ORD record: ord-bb05805260314071b7ba79f224985793
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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