Isonicotinic Acid → N-{1-(Pyridin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876316Notes

Reaction equation

HRID 876316 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:34][C:35]([F:59])([F:58])[O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[CH2:48][NH:47][CH2:46][CH:45]([NH:49][C:50](=[O:57])[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH2:44]2)=[CH:39][CH:38]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]([N:47]2[CH2:48][CH:43]([C:40]3[CH:41]=[CH:42][C:37]([O:36][C:35]([F:59])([F:34])[F:58])=[CH:38][CH:39]=3)[CH2:44][CH:45]([NH:49][C:50]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)=[O:57])[CH2:46]2)=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 5922Isonicotinic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66701272N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 66701293N-{1-(Pyridin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

51 mg (0.41 mmol) of pyridine-4-carboxylic acid together with 157 mg (0.41 mmol) of HATU and 67 mg (0.55 mmol) of 4-dimethylaminopyridine were initially charged in 2 ml of DMF, and 100 mg (0.27 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide were added. The reaction mixture was stirred overnight at RT and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 112 mg (87% of theory)

Workup

  1. custompurified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-37699f42800c4c279a78f24601fb0a18
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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