HCID 59772664, compound → HCID 59772673, compound

HRID 646233Notes

Reaction equation

HRID 646233 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25]CC3C=CC=CC=3)[CH:20]=2)([C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH:13]=2)[N:3]=1>C(O)C.[Pd]>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)([C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH:13]=2)[N:3]=1

Participants

4

Reactant 1

HCID 59772664HCID 59772664, compound

Product 1

HCID 59772673HCID 59772673, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-[3-(benzyloxy)phenyl]-3-methyl-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]-3,5-dihydro-4H-imidazol-4-one (330 mg, 0.74 mmol) and Pd/C (33 mg) in ethanol (10 ml) is hydrogenated at 45 psi overnight. After removal of the catalyst by filtration, 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 250 mg (95%). mp: 118-120° C. MS (+) ES: 354 (M+H)+.

Workup

  1. customis hydrogenated at 45 psi overnight
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate is concentrated
  5. 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-97b7ff8d29b14fb0baec72f97ef28bfb
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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