5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid → 5-(4-Chlorophenyl)-N'-(3-hydroxypropyl)-N'-methyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid hydrazide

HRID 240727Notes

Reaction equation

HRID 240727 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][CH2:38][N:39]([CH3:41])[NH2:40])(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:39]([CH2:38][CH2:37][CH2:36][OH:35])[CH3:41])=[O:22])[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 866781021-(3-((Tert-butyldimethylsilyl)oxy)propyl)-1-methylhydrazine 2,2,2-trifluoroacetate

Product 1

HCID 712941335-(4-Chlorophenyl)-N'-(3-hydroxypropyl)-N'-methyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid hydrazide

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 N-[3-(t-butyl-dimethyl-silanyloxy)-propyl]-N-methyl-hydrazine trifluoroacetate (1:1) as starting materials; the silyl protecting group was lost during reaction and work-up; LC-MS (UV peak area/ESI) 91.5%, 418.1139 (M+H)+.

Sources & evidence

ORD record
ord-67a76fa1c5764f2880e2800fcbe65970
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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