Ethyl 4-(piperazin-1-yl)benzoate → 4-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester

HRID 2190589Notes

Reaction equation

HRID 2190589 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([I:15])[CH:12]=[C:11]([F:16])[CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH2:19]([O:21][C:22](=[O:35])[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1)[CH3:20].C(OC(=O)C1C=CC(N2CCN(C3C=CC(C(=O)NC4C=CC(C)=C(I)C=4)=CN=3)CC2)=CC=1)C>>[CH2:19]([O:21][C:22](=[O:35])[C:23]1[CH:24]=[CH:25][C:26]([N:29]2[CH2:30][CH2:31][N:32]([C:2]3[CH:18]=[CH:17][C:5]([C:6](=[O:7])[NH:8][C:9]4[CH:14]=[C:13]([I:15])[CH:12]=[C:11]([F:16])[CH:10]=4)=[CH:4][N:3]=3)[CH2:33][CH2:34]2)=[CH:27][CH:28]=1)[CH3:20]

Participants

4

Reactant 3

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 593179696-Chloro-N-(3-fluoro-5-iodo-phenyl)-nicotinamideHCID 593180634-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester

Product 1

HCID 593181614-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester

Procedure

4-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester was prepared from 6-chloro-N-(3-fluoro-5-Iodo-phenyl)-nicotinamide and 4-(piperazin-1-yl)-benzoic acid ethyl ester following a method similar to the one described in the synthesis of 4-{4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester above. The product was isolated after suspension in small volume of EtOAc filtration and a wash with CH3CN. HRMS m/z calcd for C25H24N4O3FI [M+H]+: 575.0950. Found: 575.0947.

Workup

  1. customThe product was isolated after suspension
  2. filtrationin small volume of EtOAc filtration
  3. washa wash with CH3CN

Sources & evidence

ORD record
ord-89735c87745a4297b5f0d4e0d2500da7
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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