Sulfuric Acid → HCID 71128767, compound

HRID 629866Notes

Reaction equation

HRID 629866 reaction equation
[F:1][C:2]1([F:33])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH:16]4[CH2:22][CH2:21][CH:19]([CH:20]=3)[N:18](C3C=CC(OC)=CC=3)[CH2:17]4)=[CH:12][CH:13]=2)[N:8]([CH3:31])[C:7]1=[O:32].CC#N.OS(O)(=O)=O.I(O)(=O)(=O)=O>O>[CH:19]12[CH2:21][CH2:22][CH:16]([C:15]([C:11]3[N:10]=[C:9]4[N:8]([CH3:31])[C:7](=[O:32])[N:6]([CH2:5][CH:3]5[CH2:4][C:2]5([F:1])[F:33])[C:14]4=[CH:13][CH:12]=3)=[CH:20]1)[CH2:17][NH:18]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 65185Metaperiodic acidHCID 117702516HCID 117702516, compound

Product 1

HCID 71128767HCID 71128767, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-[(2,2-Difluorocyclopropyl)methyl]-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 (6-2, 52 mg, 0.12 mmol, 1.0 equiv) was added to CH3CN (1 mL) and water (1 mL). To this suspension was added aqueous H2SO4 (115 μL, 0.12 mmol, 1.0 equiv, 1.0 M) followed by periodic acid in one portion (26 mg, 0.12 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 (10-90% CH3CN:H2O) to give 6-3 as an off-white solid. MS m/z (M+H): calculated=346.4; observed=347.1.

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 (10-90% CH3CN:H2O)

Sources & evidence

ORD record
ord-2d0c1f1e32624e0b9a65018c133ae9aa
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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