Nipecotic Acid → 3-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

HRID 1642858Notes

Reaction equation

HRID 1642858 reaction equation
CN([C:4]([O:8][N:9]1N=NC2C=CC=[N:15][C:10]1=2)=[N+:5](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]([N:28]([CH2:32][CH3:33])[CH:29]([CH3:31])C)([CH3:27])C.N1CCCC(C(O)=O)C1>CN(C)C=O>[CH2:33]1[CH:31]2[CH:27]([C:4]3[O:8][N:9]=[C:10]([NH2:15])[N:5]=3)[CH2:25][N:28]([CH2:29]2)[CH2:32]1

Participants

5

Reactant 3

HCID 4498Nipecotic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon and at RT, HATU (1.2 eq.), N,N-diisopropylethylamine (2.2 eq.) and the appropriate N′-hydroxyimidamide (1.1 eq.) are added to a solution of the appropriate piperidine-3-carboxylic acid in dimethylformamide (10 ml/mmol). The reaction mixture is stirred at RT until the formation of the intermediate has gone to completion and then stirred further at 120° C. until the desired product is formed from this intermediate. The reaction mixture is then purified by preparative HPLC.

Sources & evidence

ORD record
ord-4ee5b97b5348489483f823bf15cc64eb
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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