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

HRID 876340

Reaction equation

HRID 876340 reaction equation
[C:1]([C:3]1([C:6]([OH:8])=O)[CH2:5][CH2:4]1)#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:33][C:34]([F:57])([F:56])[C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:46][NH:45][CH2:44][CH:43]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:42]2)=[CH:37][CH:36]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:1]([C:3]1([C:6]([N:45]2[CH2:46][CH:41]([C:38]3[CH:37]=[CH:36][C:35]([C:34]([F:57])([F:56])[F:33])=[CH:40][CH:39]=3)[CH2:42][CH:43]([NH:47][C:48]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)=[O:55])[CH2:44]2)=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 3

HCID 27332591-Cyanocyclopropanecarboxylic 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 66761951N-{1-[(1-Cyanocyclopropyl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

31 mg (0.28 mmol) of 1-cyanocyclopropanecarboxylic 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: 73 mg (72% of theory)

Workup

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

Sources & evidence

ORD record
ord-83e81f84ec1a47e0b06d8f17861c1cb5
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Linked notes

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