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

HRID 1748639
Notes
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Reaction equation

HRID 1748639 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86692570HCID 86692570, compound

Product 1

HCID 86692577N-[6-(1-Cyano-4-oxocyclohexyl)pyridin-3-yl]-5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamideYield 58.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes