6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide → 4-(3-Trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (3-iodo-4-methyl-phenyl)-amide

HRID 2190561Notes

Reaction equation

HRID 2190561 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([I:16])[CH:10]=2)=[O:7])=[CH:4][N:3]=1.Cl.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.IC1C=C(NC(=O)C2C=CC(N3CCOCC3)=NC=2)C=CC=1C>>[I:16][C:11]1[CH:10]=[C:9]([NH:8][C:6]([C:5]2[CH:17]=[CH:18][C:2]([N:31]3[CH2:32][CH2:33][CH:28]([C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:34])[F:35])[CH:23]=4)[CH2:29][CH2:30]3)=[N:3][CH:4]=2)=[O:7])[CH:14]=[CH:13][C:12]=1[CH3:15]

Participants

4

Reactant 3

HCID 79255626-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamideHCID 17541675N-(3-Iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamideHCID 222528494-(3-Trifluoromethylphenyl)piperidine, HCl

Product 1

HCID 593180604-(3-Trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (3-iodo-4-methyl-phenyl)-amide

Procedure

4-(3-Trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (3-iodo-4-methyl-phenyl)-amide was prepared from 6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide and 4-(3 trifluoromethyl-phenyl)piperidine hydrochloride in a manner similar to the one described in the synthesis of N-(3-iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamide above. The product was isolated after silica gel column purification with 20-40% EtOAc in hexanes. HRMS m/z calcd for C25H23N3OF3I [M+H]+: 566.0911. Found: 566.0910. START

Workup

  1. customThe product was isolated
  2. customafter silica gel column purification with 20-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-cfcb7610897c4515acab137c224fb25d
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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