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

HRID 240730Notes

Reaction equation

HRID 240730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[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][CH:36]1[CH2:39][N:38]([NH2:40])[CH2:37]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:40][N:38]3[CH2:39][CH:36]([OH:35])[CH2:37]3)=[O:21])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:17])[F:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 666869715-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acidHCID 712939753-((Tert-butyldimethylsilyl)oxy)azetidin-1-amine 2,2,2-trifluoroacetate

Product 1

HCID 712944055-(4-Chlorophenyl)-N-(3-hydroxyazetidin-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 3-(t-butyl-dimethyl-silanyloxy)-azetidin-1-ylamine trifluoroacetate (1:1) as starting materials; the silyl protecting group was lost during reaction and work-up; MS (EI) 402.2 (M+H)+.

Sources & evidence

ORD record
ord-a5286c6393884dd18ed50267108a86bd
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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