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Isobutylamine → N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutylpropionamide

HRID 13823
Notes
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Reaction equation

HRID 13823 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:12]([C:20]#[N:21])=[CH:11][C:10]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1.ClC1C(C#N)=CC(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2Cl)N=1.C(N)C(C)C.C[Mg+].[Br-].[C:61](Cl)(=[O:64])[CH2:62][CH3:63]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:61](=[O:64])[CH2:62][CH3:63])[C:12]([C:20]#[N:21])=[CH:11][C:10]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6558IsobutylamineHCID 62324Propionyl chlorideHCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrileHCID 444409945-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(isobutylamino)nicotinonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 68717477
N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutylpropionamide

Procedure

To 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile [prepared by reacting the product of Example 1 step C with isobutyl amine] (0.26 g) in TH (2.5 mL) was added MeMgBr (0.47 mL, 1.4 M solution in toluene THF 3:1) followed by propionyl chloride. After 1 hour 45 minutes the reaction was quenched with 2 M aqueous HCl, diluted with EtOAc and washed with saturated aqueous NaHCO3 solution. The dried solution (Na2SO4) was concentrated and purified via flash chromatography on silica gel eluted with 20% EtOAc in hexane affording the title compound. HPLC/MS: 486.2(M+1), 488.2 (M+3); Rt=4.60 min.

Workup

  1. customAfter 1 hour 45 minutes the reaction was quenched with 2 M aqueous HCl
  2. additiondiluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe dried solution (Na2SO4) was concentrated
  5. custompurified via flash chromatography on silica gel
  6. washeluted with 20% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-735b7ed88fb94323b68b01653e9c3a81
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