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Isobutylamine → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile

HRID 13816
Notes
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Reaction equation

HRID 13816 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[N:3]=1.[CH2:24]([NH2:28])[CH:25]([CH3:27])[CH3:26]>C1COCC1.CCOC(C)=O>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:4]1[N:3]=[C:2]([NH:28][CH2:24][CH:25]([CH3:27])[CH3:26])[C:7]([C:8]#[N:9])=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 102371012-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

Product 1

HCID 687150546-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step C EXAMPLE 26 (300 mg) in THF (3.3 mL) was added isobutylamine (0.83 mL). The reaction stirred at room temperature overnight at which point LC/MS indicated incomplete reaction. The temperature was elevated to 50° C. for 6 hours at which point the reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0% to 15% EtOAc in hexane affording the title compound. HPLC/MS: 396.1 (M+1), 398.1 (M+3); Rt=4.77 min.

Workup

  1. customreaction
  2. waitThe temperature was elevated to 50° C. for 6 hours at which
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 0% to 15% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-0bd540e1a1ed4deb903c402c40db425f
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728141B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes