Triethylamine → HCID 86680235, compound

HRID 1428806Notes

Reaction equation

HRID 1428806 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][C:4]=1[CH3:14])#[N:2].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:36]1([CH3:54])[CH:41]=[CH:40][CH:39]=[C:38]([C:42]2[C:47]([CH2:48][NH2:49])=[CH:46][CH:45]=[C:44]([C:50]([F:53])([F:52])[F:51])[N:43]=2)[CH:37]=1.C(N(CC)CC)C>C(#N)C.C(OC(=O)C)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([NH:49][CH2:48][C:47]2[C:42]([C:38]3[CH:37]=[C:36]([CH3:54])[CH:41]=[CH:40][CH:39]=3)=[N:43][C:44]([C:50]([F:53])([F:51])[F:52])=[CH:45][CH:46]=2)=[O:12])=[CH:5][C:4]=1[CH3:14])#[N:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 17910497HCID 17910497, compoundHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 86680235HCID 86680235, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-cyano-3-methylphenyl)propanoic acid (100 mg, 0.53 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (152 mg, 0.80 mmol), 1-hydroxybenzotriazole (107 mg, 0.80 mmol), (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (155 mg, 0.58 mmol) and triethylamine (0.18 mL, 1.33 mmol). The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-Cyano-3-methylphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (152 mg) was obtained as 86% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-e661d7ec14054ee98dcbc2e20afa7581
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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