HCID 59303300, compound → HCID 11206477, compound

HRID 1474512Notes

Reaction equation

HRID 1474512 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[N:21][CH:22]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[N:21][CH:22]=2)=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59303300HCID 59303300, compound

Product 1

HCID 11206477HCID 11206477, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-H-imidazole-4-carboxylic acid (4-benzyloxyphenyl)amide. (3.3 g, 11.2 mmol) in glacial acetic acid (70 mL) was hydrogenated (60 psi) over g of 10% palladium on carbon (0.3 g) at 25° C. for 18 hours. The catalyst was removed by filtration, and the solvent was evaporated in vacuo. The residue was stirred with NaHCO3 solution and the solid collected. There was obtained 2.4 g (100% yield) of the title compound as a yellow solid. MS m/z 204 (MH+). 1H NMR(DMSO-d6) δ 6.7 (dd, 2H), 7.5 (dd, 2H), 7.7 (s, 1H), 7.8 (s, 1H), 9.1 (s, 1H), 9.6 (s, 1H) and 12.5 (s, 1H).

Workup

  1. customat 25° C.
  2. customfor 18 hours
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated in vacuo
  5. customthe solid collected

Sources & evidence

ORD record
ord-19070cb3470b46f09430cb3eced03cc4
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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