Propylamine → N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-propylpropionamide

HRID 13831

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][CH2:17][CH3:18])[C:12]([C:19]#[N:20])=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.ClC1C(C#N)=CC(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2Cl)N=1.C(N)CC.C[Mg+].[Br-].[C:59](Cl)(=[O:62])[CH2:60][CH3:61]>>[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][CH2:17][CH3:18])[C:59](=[O:62])[CH2:60][CH3:61])[C:12]([C:19]#[N:20])=[CH:11][C:10]=1[C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1

Participants

Reactant 5

HCID 7852Propylamine

HCID 62324Propionyl chloride

HCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

HCID 687184456-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-(propylamino)pyridine-3-carbonitrile

HCID 178418689HCID 178418689, compound

Product 1

HCID 68718623N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-propylpropionamide

Procedure

6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-(propylamino)pyridine-3-carbonitrile (prepared by reaction of the product of Step C Example 1 with propylamine using the procedure of Step D EXAMPLE 26) was reacted with MeMgBr followed by propionyl chloride using the procedure of EXAMPLE 42 Step A to afford the title compound. HPLC/MS: 472.1 (M+1), 474.1 (M+3); Rt=4.40 min.

Sources & evidence

ORD record: ord-343535a0b1044b68b862867a52f92f28
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728141B2

Linked notes

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