5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid → 5-(4-Chlorophenyl)-N-(4-(2-hydroxyethyl)piperidin-1-yl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxamide

HRID 240717Notes

Reaction equation

HRID 240717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([OH:22])=O)[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([Si](C)(C)[O:35][CH2:36][CH2:37][CH:38]1[CH2:43][CH2:42][N:41]([NH2:44])[CH2:40][CH2:39]1)(C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([NH:44][N:41]3[CH2:42][CH2:43][CH:38]([CH2:37][CH2:36][OH:35])[CH2:39][CH2:40]3)=[O:22])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 666869715-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acidHCID 712943124-(2-((Tert-butyldimethylsilyl)oxy)ethyl)piperidin-1-amine 2,2,2-trifluoroacetate

Product 1

HCID 712939485-(4-Chlorophenyl)-N-(4-(2-hydroxyethyl)piperidin-1-yl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxamide

Procedure

The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (CAN 1018782-82-5) and 4-[2-(t-butyl-dimethyl-silanyloxy)-ethyl]-piperidin-1-ylamine trifluoroacetate (1:1) as starting materials; the silyl protecting group was lost during reaction and work-up; LC-MS (UV peak area/ESI) 94.9%, 458.1448 (M+H)+.

Sources & evidence

ORD record
ord-4d5bf9e8f4b64995acd228a40446fd78
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

Loading…