HCID 59772746, compound → HCID 59772721, compound

HRID 2220443Notes

Reaction equation

HRID 2220443 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]CC3C=CC=CC=3)[CH:15]=2)([C:9]2[CH:13]=[CH:12][NH:11][CH:10]=2)[N:3]=1>C(O)C.[Pd]>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)([C:9]2[CH:13]=[CH:12][NH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 1

HCID 59772746HCID 59772746, compound

Product 1

HCID 59772721HCID 59772721, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-(3-benzyloxyphenyl)-5-(1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (70 mg, 0.2 mmol) and Pd/C (8 mg) in ethanol (10 ml) is hydrogenated at 45 psi overnight. The catalyst is removed by filtration and the filtrate is concentrated. The crude material is purified by flash chromatography (silica gel, EtOAc/2.0M ethanolic NH3: 90/10 to 80/20) to afford the title compound as a solid, 49 mg (93%) mp 142-145° C., MS (+) ES: 271 (M+H)+.

Workup

  1. customis hydrogenated at 45 psi overnight
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe crude material is purified by flash chromatography (silica gel, EtOAc/2.0M ethanolic NH3: 90/10 to 80/20)

Sources & evidence

ORD record
ord-6a0dfaeea8404b2ab5ce7eb8be87d50a
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

Loading…