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

1,2-Dichloroethane → N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzyl}-1-trifluoromethyl-cyclopropaneamide

HRID 1258697
Notes
Print preview

Reaction equation

HRID 1258697 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N:19]=[C:20]=S.[Cl:22][C:23]1[C:24]([N:32]2[CH2:37][CH2:36][CH:35]([C:38]([F:41])([F:40])[F:39])[CH2:34][CH2:33]2)=[CH:25][C:26]([NH:30][CH3:31])=[C:27]([CH:29]=1)[NH2:28].C(Cl)CCl>CN(C=O)C.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[NH:19][C:20]1[N:30]([CH3:31])[C:26]2[CH:25]=[C:24]([N:32]3[CH2:37][CH2:36][CH:35]([C:38]([F:40])([F:41])[F:39])[CH2:34][CH2:33]3)[C:23]([Cl:22])=[CH:29][C:27]=2[N:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 679581715-Chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)anilineHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 86674337N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzyl}-1-trifluoromethyl-cyclopropaneamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (0.15 g; 0.45 mmol) and 5-chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline (0.14 g; 0.45 mmol) in DMF (3 mL) was stirred overnight at rt. EDC (0.086 g; 0.45 mmol) was added and the mixture was heated to 90° C. for 1 h. The mixture was poured in water, extracted with DCM and the combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by column chromatography.

Workup

  1. temperaturethe mixture was heated to 90° C. for 1 h
  2. extractionextracted with DCM
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-f09a456475d549c29b2b9ed8410d5af1
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466186B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes