Norbornadiene → HCID 10427878, compound

HRID 456789Notes

Reaction equation

HRID 456789 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:21]=[C:20]([C:22]#[N:23])[N:19]([CH3:24])[N:18]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:25]12CC(C=C1)C=[CH:26]2>O1CCOCC1>[CH3:24][N:19]1[C:20]([C:22]#[N:23])=[CH:21][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:7]3[CH2:6][C@H:5]([CH2:4][N:1]4[CH:26]=[CH:25][N:3]=[N:2]4)[O:9][C:8]3=[O:10])=[CH:12][CH:13]=2)=[N:18]1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 586252013-{4-[(5R)-5-(Azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-1-methyl-1H-pyrazole-5-carbonitrile2×

Product 1

HCID 10427878HCID 10427878, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

3-{4-[(5R)-5-(Azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-1-methyl-1H-pyrazole-5-carbonitrile (Intermediate 14, 00 mg, 0.62 mmol), bicyclo[2.2.1]hepta-2,5-diene (0.70 ml, 6.50 mmol) and dioxane (5 ml) were combined and warmed to 90° C. for 8 hours. The mixture was evaporated and purified by chromatography on silica gel eluting with ethyl acetate to give the title compound as an off-white solid (110 mg).

Workup

  1. customThe mixture was evaporated
  2. custompurified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-7c1e96db7b174ddab79a438e898756c6
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

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