Norborn-2-ylacetic acid → 1-(Bicyclo[2.2.1]hept-2-ylacetyl)-4-[3-(trifluoromethyl)pyridin-2-yl]piperazine

HRID 1868110

Reaction equation

HRID 1868110 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[CH:17]12[CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]2[CH2:24][C:25](O)=[O:26].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH:17]12[CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]2[CH2:24][C:25]([N:12]1[CH2:11][CH2:10][N:9]([C:4]2[C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13]1)=[O:26]

Participants

5

Reactant 3

HCID 79139Norborn-2-ylacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazine

Product 1

HCID 685521491-(Bicyclo[2.2.1]hept-2-ylacetyl)-4-[3-(trifluoromethyl)pyridin-2-yl]piperazineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Coupling of 1-(3-(trifluoromethyl)pyridin-2-yl)piperazine (271 mg, 1.17 mmol) with 2-(bicyclo[2.2.1]heptan-2-yl)acetic acid (100 mg, 0.65 mmol) was carried out according to a similar procedure described for example 19A using N,N-dimethylformamide (1 mL) as solvent and benzotriazole-1 yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (700 mg, 1.56 mmol) as coupling agent. 1-(bicyclo[2.2.1]hept-2-ylacetyl)-4-[3-(trifluoromethyl)pyridin-2-yl]piperazine was obtained in 82% yield (195 mg) as colorless oil.

Sources & evidence

ORD record
ord-7f6132978a0347089cab39391db43e51
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Linked notes

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