N-Benzyl-2-azabicyclo[2.2.1]heptan-7-one → 4-(4-((1SR,4SR,7RS)-2-azabicyclo[2.2.1]heptan-7-ylamino)phenyl)-1,2,5-oxadiazol-3-amine

HRID 75688Notes

Reaction equation

HRID 75688 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:13])=[N:10][O:11][N:12]=2)=[CH:4][CH:3]=1.C([N:21]1[CH2:26][CH:25]2[C:27](=O)[CH:22]1[CH2:23][CH2:24]2)C1C=CC=CC=1>>[CH:22]12[CH:27]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:8]4[C:9]([NH2:13])=[N:10][O:11][N:12]=4)=[CH:6][CH:7]=3)[CH:25]([CH2:24][CH2:23]1)[CH2:26][NH:21]2

Participants

3

Reactant 2

HCID 49759181N-Benzyl-2-azabicyclo[2.2.1]heptan-7-oneHCID 59799786HCID 59799786, compound

Product 1

HCID 672356774-(4-((1SR,4SR,7RS)-2-azabicyclo[2.2.1]heptan-7-ylamino)phenyl)-1,2,5-oxadiazol-3-amine

Procedure

Reaction of 4-(4-aminophenyl)-1,2,5-oxadiazol-3-amine with 2-benzyl-2-azabicyclo[2.2.1]heptan-7-one (J. R. Malpass, S. Handa, and R. White, Org. Lett., 2005, 7, 2759-2762) affords the title compound as the benzyl-protected amine. Purification by chromatography followed by removal of the benzyl group by hydrogenolysis affords the title amine.

Sources & evidence

ORD record
ord-ccb3e869093e4bfd9fa8ab8e17e4d9a1
Source dataset
uspto-grants-2014_09
Patent number
US08835457B2

Reaction notes

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