2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(4-hydroxybut-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(4-hydroxybutyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30576Notes

Reaction equation

HRID 30576 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:22][CH:21]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH2:17][CH2:18][OH:19])[CH:10]=2)[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:24][CH:25]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=2)[N:3]=1

Participants

5

Reactant 2

HCID 161141522-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(4-hydroxybut-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 161141532-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(4-hydroxybutyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-oneYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of a solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(4-hydroxybut-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.26 g, 0.65 mmol) in ethanol and 5% palladium on charcoal (26 mg) was placed on a Paar hydrogenator at 40 psi hydrogen for 8 hrs. The reaction mixture was filtered through a celite pad. The filtrate was concentrated in vacuo. The resultant residue was purified by flash chromatography on silica gel, 5% methanol/ ethyl acetate as eluent, to give the title product as a white solid, 0.16 g (61% yield), mp 63-66° C.; 1H NMR (DMSO-d6) δ 1.4 ((2H, 2H); 1.5 (m, 1 H); 2.5 (2H, under DMSO peak) 2.95 (s, 3 H); 3.3 (q, 2 H); 4.3 (t, 1 H); 6.6 (b, 2H); 7.1 (m, 3H); 7.15 (t, 2F); 7.2 (m, 3 H); 7.4 (d, 2 H); MS [(+)ESI] m/z=404 [M−H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe resultant residue was purified by flash chromatography on silica gel, 5% methanol/ ethyl acetate as eluent

Sources & evidence

ORD record
ord-3c49852dca704a8e90cedc10ce2f8a06
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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