Pyridine → n-{4-Chloro-2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamide

HRID 12171

Reaction equation

HRID 12171 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=1)=[O:22].N1C=CC=CC=1>S(Cl)(Cl)=O.ClCCl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:4]([C:3]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:2]=2[F:1])=[O:6])=[C:15]([C:21](=[O:22])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 5906594-Cyano-2-fluorobenzoic acidHCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 10181017n-{4-Chloro-2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamideYield 111.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-fluoro-4-cyanobenzoic acid (1 g, 6.06 mmol) in thionyl chloride (5 ml) was refluxed for 2 hr. After concentration, the residue was dissolved in dichloromethane (5 ml). And a solution of the compound of (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (1.2 g, 4.25 mmol) in dichloromethane (10 ml) and pyridine (1.47 ml, 18.18 mmol) were added. The mixture was stirred at r.t. overnight. The precipitate was filtered and washed with a little amount of dichloromethane to give N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamide (2.03 g, 78%). MS found for C20H11Cl2FN4O2 M+=429, (M+2)+=431.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. filtrationThe precipitate was filtered
  4. washwashed with a little amount of dichloromethane

Sources & evidence

ORD record
ord-48fd1d68fa0249118488f86d53172bd6
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Linked notes

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