2-Azabicyclo[2.2.1]hept-5-ene → HCID 25192136, compound

HRID 2382627Notes

Reaction equation

HRID 2382627 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=O)[NH:2]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C12CC(C=C1)CN2.[N:22]1[O:23][N:24]=[C:25]2[CH:30]=[C:29]([C:31](Cl)=[O:32])[CH:28]=[CH:27][C:26]=12>>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][N:2]2[C:31]([C:29]1[CH:28]=[CH:27][C:26]2=[N:22][O:23][N:24]=[C:25]2[CH:30]=1)=[O:32]

Participants

5

Reactant 4

HCID 1388052-Azabicyclo[2.2.1]hept-5-eneHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-oneHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 25192136HCID 25192136, compound

Procedure

Prepared from 2-azabicyclo[2.2.1]hept-5-en-3-one by reducing with LiAlH4 and then coupling the resultant 2-azabicyclo[2.2.1]hept-5-ene with [2,1,3]-benzoxadiazole-5-carbonylchloride as described for Example 7. The title product was isolated as a white solid after crystallization from MTBE/hexane: mp=106-108° C., LC-MS, MH+=242.25; 1H NMR (300 MHz, CDCl3, rotamers) δ 7.98-7.86 (m, 2H), 7.58-7.53 (m, 1H), 6.60-6.50 (m, 1H), 6.36-6.32 (m, 1H), 5.25 and 4.57 (s, total 1H), 3.67-3.62 (m, 1H), 3.39 and 3.32 (s, total 1H), 3.03 and 2.70 (both d, J=10.2 and 8.7 Hz respectively, total 1H), 1.75 ppm (s, 2H).

Sources & evidence

ORD record
ord-f9c7d1890949424f88e83d5522c7334f
Source dataset
uspto-grants-2012_09
Patent number
US08263591B2

Reaction notes

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