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

HRID 30579Notes

Reaction equation

HRID 30579 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][O:18][CH3:19])[CH:10]=2)[N:3]=1>[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][O:18][CH3:19])[CH:10]=2)[N:3]=1

Participants

3

Reactant 1

HCID 574358862-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

Product 1

HCID 161142522-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxypropyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-oneYield 40%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of an ethanolic solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.1 g, 0.25 mmol) and 10% palladium on charcoal (10 mg) was placed under a hydrogen filled balloon for 16 h and filtered thru celite. The filtrate was concentrated to dryness in vacuo. The resultant residue was purified by flash chromatography on silica gel, ethyl acetate as eluent, to give the title product as a white solid, 0.04 g (40% yield), mp 48-50° C.; 1H NMR (DMSO-d6) δ 2.4 (m, 2H); 2.95 (s, 3H); 3.2 (s, 3H); 3.3 (t, 2H); 6.6 (b, 2H); 7.1 (m, 3H); 7.2 (m, 4H); 7.4 (d, 2H); MS [(+)ESI] m/z=404 [M−H]+.

Workup

  1. customfor 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness in vacuo
  4. customThe resultant residue was purified by flash chromatography on silica gel, ethyl acetate as eluent

Sources & evidence

ORD record
ord-f63714413e8d4eeea544ecc2eb22c284
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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