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Trifluoroacetic acid → 1-[5-({[5-methyl 1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-4-oxocyclohexanecarboxylic acid ethyl ester

HRID 1748636
Notes
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Reaction equation

HRID 1748636 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[CH:33]=[N:34][N:35]([C:38]4[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=4)[C:36]=3[CH3:37])=[O:31])=[CH:25][N:24]=2)[CH2:22][CH2:21][C:16]2(OCC[O:17]2)[CH2:15][CH2:14]1)=[O:12])[CH3:9]>ClCCl>[CH2:8]([O:10][C:11]([C:13]1([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[CH:33]=[N:34][N:35]([C:38]4[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][CH:43]=4)[C:36]=3[CH3:37])=[O:31])=[CH:25][N:24]=2)[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]1)=[O:12])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 866925638-[5-({[5-Methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester

Product 1

HCID 866925731-[5-({[5-methyl 1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-4-oxocyclohexanecarboxylic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Trifluoroacetic acid (0.96 ml) was added at room temperature to a solution of 8-[5-({[5-methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester (1.27 g) described in Example D4 in dichloromethane (2.5 ml) and stirred at the same temperature for six hours. Trifluoroacetic acid (1.9 ml) was added at the same temperature and stirred at the same temperature for 18 hours. After the reaction, the solvent and trifluoroacetic acid were evaporated, a saturated aqueous solution of sodium bicarbonate was added and extracted with ethyl acetate twice. The organic solution was dried over anhydrous magnesium sulfate and concentrated to give 1-[5-({[5-methyl 1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-4-oxocyclohexanecarboxylic acid ethyl ester (1.09 g) as a white solid.

Workup

  1. stirringstirred at the same temperature for 18 hours
  2. customAfter the reaction
  3. customthe solvent and trifluoroacetic acid were evaporated
  4. additiona saturated aqueous solution of sodium bicarbonate was added
  5. extractionextracted with ethyl acetate twice
  6. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e39cfae10ee4b959e0ee0fdb6300bc9
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150555B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes