3-Methyl-isonicotinic acid → N-{1-[(3-Methylpyridin-4-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876341

Reaction equation

HRID 876341 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:35][C:36]([F:59])([F:58])[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>[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([N:47]1[CH2:48][CH:43]([C:40]2[CH:39]=[CH:38][C:37]([C:36]([F:59])([F:58])[F:35])=[CH:42][CH:41]=2)[CH2:44][CH:45]([NH:49][C:50]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[O:57])[CH2:46]1)=[O:10]

Participants

6

Reactant 3

HCID 15020033-Methyl-isonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66701397N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 66762085N-{1-[(3-Methylpyridin-4-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

38 mg (0.28 mmol) of 3-methylpyridine-4-carboxylic acid together with 131 mg (0.34 mmol) of HATU and 56 mg (0.46 mmol) of 4-dimethylaminopyridine were initially charged in 2 ml of DMF, and 80 mg (0.23 mmol) of N-{5-[4-(trifluoromethyl)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: 65 mg (59% of theory)

Workup

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

Sources & evidence

ORD record
ord-cef5649329494c15b9cfb79dcd182636
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Linked notes

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