Sulfuric Acid → HCID 71135235, compound

HRID 629870Notes

Reaction equation

HRID 629870 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]4[CH2:21][CH2:20][CH:17]([C:18]=3[CH3:19])[N:16](C3C=CC(OC)=CC=3)[CH2:15]4)=[CH:10][CH:11]=2)[N:6]([CH3:30])[C:5]1=[O:31].CC#N.OS(O)(=O)=O.I(O)(=O)(=O)=O>O>[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]4[CH2:21][CH2:20][CH:17]([C:18]=3[CH3:19])[NH:16][CH2:15]4)=[CH:10][CH:11]=2)[N:6]([CH3:30])[C:5]1=[O:31]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 65185Metaperiodic acidHCID 1177023811-(2,2-Dimethylpropyl)-5-[2-(4-methoxyphenyl)-6-methyl-2-azabicyclo-[2.2.2]oct-5-en-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 71135235HCID 71135235, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-(2,2-Dimethylpropyl)-5-[2-(4-methoxyphenyl)-6-methyl-2-azabicyclo-[2.2.2]oct-5-en-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (7-3, 40.3 mg, 0.09 mmol, 1.0 equiv) was added to CH3CN (820 μL) and water (820 μL). To this suspension was added aqueous H2SO4 (90 μL, 0.09 mmol, 1.0 equiv, 1.0 M) followed by periodic acid in one portion (21 mg, 0.09 mmol, 1.0 equiv). The reaction contents were heated to 50° C. for 18 h. Following this duration, LCMS showed consumption of starting material. The mixture was subsequently filtered through Celite, rinsed with CH3CN and purified by reverse-phase HPLC (15-90% CH3CN:0.1% TFA in H2O) to give 7-4 as a tan solid.

Workup

  1. customThe reaction contents
  2. customconsumption of starting material
  3. filtrationThe mixture was subsequently filtered through Celite
  4. washrinsed with CH3CN
  5. custompurified by reverse-phase HPLC (15-90% CH3CN:0.1% TFA in H2O)

Sources & evidence

ORD record
ord-87b5e47252f8462cbe9cce712329293f
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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