Sulfuric Acid → 5-(2-Azabicyclo[2.2.2]oct-5-en-5-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629860Notes

Reaction equation

[CH3:1][C:2]([CH3:32])([CH3:31])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]4[CH2:20][CH2:19][CH:17]([CH:18]=3)[N:16](C3C=CC(OC)=CC=3)[CH2:15]4)=[CH:10][CH:11]=2)[N:6]([CH3:29])[C:5]1=[O:30].CC#N.OS(O)(=O)=O.I(O)(=O)(=O)=O>O>[CH:17]12[CH2:19][CH2:20][CH:14]([C:13]([C:9]3[N:8]=[C:7]4[N:6]([CH3:29])[C:5](=[O:30])[N:4]([CH2:3][C:2]([CH3:31])([CH3:32])[CH3:1])[C:12]4=[CH:11][CH:10]=3)=[CH:18]1)[CH2:15][NH:16]2

Participants

Conditions

Temperature: 50 °C

Procedure

1-(2,2-Dimethylpropyl)-5-[2-(4-methoxyphenyl)-2-azabicyclo[2.2.2]oct-5-en-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2-4, 339 mg, 0.78 mmol, 1.0 equiv) was added to CH3CN (7 mL) and water (7 mL) To this suspension was added aqueous H2SO4 (0.78 mL, 0.78 mmol, 1.0 equiv, 1.0 M) followed by periodic acid in one portion (179 mg, 0.78 mmol, 1.0 equiv). The reaction contents were heated to 50° C. for 18 h. Following this duration,

Workup

customThe reaction contents

Sources & evidence

ORD record: ord-97c6c2e867d64a98a8516bd6bbde74bd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315518B2

Reaction notes

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