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Potassium Carbonate → 3-(3-(4-(Piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acid

HRID 625268
Notes
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Reaction equation

HRID 625268 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:41]=[CH:42][CH:43]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:11][C:10]=1[C:21]1[CH:22]=[C:23]([CH:38]=[CH:39][N:40]=1)[C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)=[O:25])=[O:7].[SH:44][C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][CH:53]=1)[C:48]([OH:50])=[O:49].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N:15]1([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]([C:5]3[CH:4]=[C:3]([CH:43]=[CH:42][CH:41]=3)[CH2:2][S:44][C:45]3[CH:46]=[C:47]([CH:51]=[CH:52][CH:53]=3)[C:48]([OH:50])=[O:49])=[O:7])=[C:10]([C:21]3[CH:22]=[C:23]([C:24](=[O:25])[NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=4)[CH:38]=[CH:39][N:40]=3)[CH:11]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 665867362-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamide

Product 1

HCID 665867593-(3-(4-(Piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acidYield 37.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 250 mg of 2-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamide 8.1a, 70 mg of 3-mercaptobenzoic acid, 10 mL of acetone, and 171 mg of K2CO3 was stirred for 16 h and then filtered. The solvent was removed by evaporation. The residue was dissolved in dichloromethane and the resulting solution was washed with aqueous hydrochloric acid. The solution was dried, and the solvent was evaporated. The residue was purified by silica gel chromatography to give 113 mg of product. MS (ES, m/z) 725 [M+H]+.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed by evaporation
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe resulting solution was washed with aqueous hydrochloric acid
  5. customThe solution was dried
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-316e0cafbec048939880cb2ae95551e0
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09301951B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes