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

HRID 661265Notes

Reaction equation

HRID 661265 reaction equation
N1CCCC(C(O)=O)C1.CN([C:13]([O:17][N:18]1N=NC2C=CC=[N:24][C:19]1=2)=[N+:14](C)C)C.F[P-](F)(F)(F)(F)F.[CH:34]([N:37]([CH2:41][CH3:42])[CH:38]([CH3:40])C)([CH3:36])C>CN(C)C=O>[CH2:42]1[CH:40]2[CH:36]([C:13]3[O:17][N:18]=[C:19]([NH2:24])[N:14]=3)[CH2:34][N:37]([CH2:38]2)[CH2:41]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

A solution of the appropriate piperidine-3-carboxylic acid in dimethylformamide (10-20 ml/mmol) is admixed under argon at RT with HATU (1.2 eq.), N,N-diisopropylethylamine (2.2 eq.) and the appropriate alkyl N′-hydroxyimidocarbamate (1.1 eq.). The reaction mixture is stirred at RT until the formation of the intermediate is complete and then stirred further at 120° C. until the desired product is formed from this intermediate. The reaction mixture is then purified by means of preparative HPLC.

Sources & evidence

ORD record
ord-f341009dd86d4fdd93b6ed168bbae2dc
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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