Furfurylamine → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-(3-{[(2-furylmethyl)-amino]methyl}phenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 2240977Notes

Reaction equation

HRID 2240977 reaction equation
[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]([C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=O)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)[N:6]=1.[CH2:27]([NH2:33])[C:28]1[O:32][CH:31]=[CH:30][CH:29]=1.[BH4-].[Na+].[OH-].[Na+]>CO>[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)([C:17]2[CH:24]=[CH:23][CH:22]=[C:19]([CH2:20][NH:33][CH2:27][C:28]3[O:32][CH:31]=[CH:30][CH:29]=3)[CH:18]=2)[N:6]=1

Participants

6

Reactant 4

HCID 3438FurfurylamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 16113437HCID 16113437, compound

Product 1

HCID 251263142-amino-5-[4-(difluoromethoxy)phenyl]-5-(3-{[(2-furylmethyl)-amino]methyl}phenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-oneYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A small vial (2 ml) was charged with 3-[2-amino-4-(4-difluoromethoxy-phenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-benzaldehyde (110 mg, 306 μmol). To this was added furfurylamine (30 mg, 308 μmol) in methanol (1 ml). After stirring overnight at room temperature sodium borohydride (29 mg) was added, then after another 90 minutes 1N sodium hydroxide (1 ml) was added and the mixture extracted with diethyl ether. The ethereal layer was concentrated by rotary evaporation, diluted with methanol and re-concentrated (repeated three times). Finally the oily residue was redissolved in diethylether/hexanes and concentrated, twice then placed under vacuum to give a white foam 96 mg (71%) 1H NMR (400 MHz, DMSO-d6) δ ppm 2.94 (s, 3H) 3.56 (br. s., 4H) 6.15 (d, J=3.2 Hz, 1H) 6.68 (br. s., 1H) 6.34 (t, J=2.4 Hz, 1H) 6.64 (s, 2H) 7.06 (d, J=8.8 Hz, 2H) 7.13 (t, J=74.18 Hz, 1H) 7.15-7.28 (m, 3H) 7.37 (s, 1H) 7.43 (d, J=8.8 Hz 2H) 7.51 (t, J=1.4 Hz, 1H); MS (ES) m/z 439.2 [M−H]−

Workup

  1. additionwas added
  2. extractionthe mixture extracted with diethyl ether
  3. concentrationThe ethereal layer was concentrated by rotary evaporation
  4. additiondiluted with methanol
  5. concentrationre-concentrated (repeated three times)
  6. dissolutionFinally the oily residue was redissolved in diethylether/hexanes
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca13e117a8a74e67a8aef5deae85cb64
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

Loading…