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Triethylamine → 2-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428782
Notes
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Reaction equation

HRID 1428782 reaction equation
CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:22]1([CH3:40])[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH:23]=1.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH:49]([CH3:53])[C:50](O)=[O:51])=[CH:45][C:44]=1[F:54])#[N:42].C(N(CC)CC)C>>[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH:49]([CH3:53])[C:50]([NH:35][CH2:34][C:33]2[C:28]([C:24]3[CH:23]=[C:22]([CH3:40])[CH:27]=[CH:26][CH:25]=3)=[N:29][C:30]([C:36]([F:37])([F:39])[F:38])=[CH:31][CH:32]=2)=[O:51])=[CH:45][C:44]=1[F:54])#[N:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 183667732-(4-Cyano-3-fluorophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 86680225
2-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Procedure

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.5 equiv), 1-hydroxybenzotriazole (1.5 equiv), and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (1 equiv) are added to a solution of 2-(4-cyano-3-fluorophenyl)propanoic acid (5 equiv) drop-wise triethylamine (2.5 equiv). The reaction mixture is stirred overnight at room temperature. The reaction is quenched with water and extracted with ethyl acetate. The extracted organic layer is dried over magnesium sulfate. After evaporate solvent, purified by column chromatographic purification (ethylacetate:hexane) afforded 2-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide.

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracted organic layer is dried over magnesium sulfate
  4. customAfter evaporate solvent
  5. custompurified by column chromatographic purification (ethylacetate:hexane)

Sources & evidence

ORD record
ord-96b3bc4000ad473ba21275967bf98974
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes