HCID 59772746, compound → HCID 59772721, compound

HRID 646221Notes

Reaction equation

HRID 646221 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-1b61de65e01246929c216c33af1f829e
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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