Lithium Hydroxide → HCID 44547649, compound

HRID 1517127Notes

Reaction equation

HRID 1517127 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:5][C:4]([CH3:19])=[C:3]1[C:20](O)=[O:21].COC(C1C(C)=CC(C2C=CC=C(C(F)(F)F)C=2)=C(O)N=1)=O.CI.C(=O)([O-])[O-].[Cs+].[Cs+].COC(C1N(C)C(=O)C(C2C=CC=C(C(F)(F)F)C=2)=CC=1C)=O.[OH-].[Li+].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[N:89]1([CH:94]2[CH2:99][CH2:98][NH:97][CH2:96][CH2:95]2)[CH2:93][CH2:92][CH2:91][CH2:90]1>CN(C=O)C.C1COCC1.CO.C(Cl)Cl>[CH3:1][N:2]1[C:3]([C:20]([N:97]2[CH2:98][CH2:99][CH:94]([N:89]3[CH2:93][CH2:92][CH2:91][CH2:90]3)[CH2:95][CH2:96]2)=[O:21])=[C:4]([CH3:19])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)[C:7]1=[O:8]

Participants

12

Reactant 8

HCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 787034-(1-Pyrrolidinyl)piperidineHCID 57441171HCID 57441171, compoundHCID 57441172HCID 57441172, compoundHCID 670252896-Hydroxy-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester2×HCID 86637422HCID 86637422, compound

Product 1

HCID 44547649HCID 44547649, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In analogy to the procedure described for the preparation of example 13, 1,3-dimethyl-6-oxo-5-(3-trifluoromethyl-phenyl)-1,6-dihydro-pyridine-2-carboxylic acid [prepared by i) reaction of 6-hydroxy-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester; 3-methyl-6-oxo-5-(3-trifluoromethyl-phenyl)-1,6-dihydro-pyridine-2-carboxylic acid methyl ester (tautomers, intermediate 15B) with methyl iodide, cesium carbonate in DMF in analogy to the procedure described for the preparation of intermediate 5F; ii) saponification of the thus formed 1,3-dimethyl-6-oxo-5-(3-trifluoromethyl-phenyl)-1,6-dihydro-pyridine-2-carboxylic acid methyl ester with lithium hydroxide in THF/MeOH in analogy to the procedure described for the preparation of intermediate 5G] was reacted with oxalyl chloride/DMF in CH2Cl2 followed by treatment with 4-pyrrolidin-1-yl-piperidine to give the title compound as colorless solid. MS: 448.2 (MH+).

Workup

  1. customprepared by i)

Sources & evidence

ORD record
ord-4567de1263744c5285b1562c3bf7ccf0
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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