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

1,2-Dichloroethane → N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyano-3-fluorophenyl)propanamide

HRID 1843038
Notes
Print preview

Reaction equation

HRID 1843038 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[F:14])#[N:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[Cl:29][C:30]1[CH:31]=[C:32]([N:36]2[C:40]([CH2:41][NH2:42])=[CH:39][C:38]([C:43]([F:46])([F:45])[F:44])=[N:37]2)[CH:33]=[CH:34][CH:35]=1>C(#N)C.O>[Cl:29][C:30]1[CH:31]=[C:32]([N:36]2[C:40]([CH2:41][NH:42][C:10](=[O:12])[CH:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:14])[CH:5]=3)[CH3:13])=[CH:39][C:38]([C:43]([F:44])([F:45])[F:46])=[N:37]2)[CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 183667732-(4-Cyano-3-fluorophenyl)propanoic acidHCID 66644230(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine

Product 1

HCID 70816495N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyano-3-fluorophenyl)propanamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-cyano-3-fluorophenyl)propanoic acid (440 mg, 2.278 mmol) in acetonitrile was added HOBt (462 mg, 3.417 mmol), EDC (655 mg, 3.417 mmol) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (659 mg, 2.392 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was added water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to give pure compound N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyano-3-fluorophenyl)propanamide (870 mg, 85%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8ee084ef1cc6474ba60c01cdebbc26b3
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946204B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes