HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1428746
Notes
Print preview

Reaction equation

HRID 1428746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C:15]1([CH3:33])[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[N:22]=2)[CH:16]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([NH:28][CH2:27][C:26]2[C:21]([C:17]3[CH:16]=[C:15]([CH3:33])[CH:20]=[CH:19][CH:18]=3)=[N:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 708476592-(3-Chloro-4-cyanophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 86680216
2-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
Yield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-chloro-4-cyanophenyl)propanoic acid (95 mg, 0.454 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (121 mg, 0.454 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (131 mg, 0.681 mmol), 1-hydroxybenzotriazole (92 mg, 0.681 mmol) and triethylamine (0.16 mL, 1.135 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate 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-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (182 mg) was obtained as 88% 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-91607e5b2b1948aeafad9c02a777f2ed
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes