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 240721Notes

Reaction equation

HRID 240721 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.F[C:24](F)(F)[C:25]([OH:27])=O.C([SiH2]OC(C)(C)[CH:37]1[CH2:42][CH2:41][N:40]([NH2:43])[CH2:39][CH2:38]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:43][N:40]3[CH2:41][CH2:42][CH:37]([CH2:24][CH2:25][OH:27])[CH2:38][CH2:39]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 1317311944-(t-Butyl-dimethyl-silanyloxymethyl)-piperidin-1-ylamine 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-(t-butyl-dimethyl-silanyloxymethyl)-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) 96.6%, 444.1292 (M+H)+.

Sources & evidence

ORD record
ord-d5ad7c965ead429ebb79d73d8a02b7d4
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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