HCID 59257847, compound → HCID 86629737, compound

HRID 551066Notes

Reaction equation

HRID 551066 reaction equation
Cl[C:2]1[C:7]2[N:8]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9](=[O:16])[N:10]([CH2:11][C:12](OC)=[O:13])[C:6]=2[C:5]([N+:22]([O-])=O)=[C:4](Cl)[N:3]=1>CO.[Pd]>[O:16]=[C:9]1[N:10]2[C:6]3[C:5]([NH:22][C:12](=[O:13])[CH2:11]2)=[CH:4][N:3]=[CH:2][C:7]=3[N:8]1[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 1

HCID 59257847HCID 59257847, compound

Product 1

HCID 86629737HCID 86629737, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of dimethyl 2,2′-(4,6-dichloro-7-nitro-2-oxo-1H-imidazo[4,5-c]pyridine-1,3-diyl)diacetate (40 mg, 0.10 mmol) from Step E and 10% Pd/C (12 mg) in MeOH (2 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm) for 6 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The crude material was heated at 80° C. for 2 h in toluene (2 mL) and AcOH (2 mL) then concentrated to give the title compound. MS: m/z=263 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. concentrationAcOH (2 mL) then concentrated

Sources & evidence

ORD record
ord-5165c17775d24e9183fe3a58651f9972
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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