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

HRID 2240974Notes

Reaction equation

HRID 2240974 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]([NH2:30])[CH2:28][CH3:29].[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:30][CH2:27][CH2:28][CH3:29])[CH:18]=2)[N:6]=1

Participants

6

Reactant 4

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 16113437HCID 16113437, compound

Product 1

HCID 251263152-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-{3-[(propyl-amino)methyl]phenyl}-3,5-dihydro-4H-imidazol-4-oneYield 79.2%

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 (32.7 mg, 91.0 μmol). To this was added one-fifth of a solution of propylamine (31 mg, 0.524 mmol) in methanol (2.50 ml). After stirring for two hours sodium borohydride (8.7 mg) was added, then after another hour 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 29 mg (78%) 1H NMR (400 MHz, DMSO-d6) δ ppm 0.79 (t, J=7.3 Hz, 3H) 1.29-1.39 (m, 2H) 2.36 (t, J=7.1 Hz, 2H) 2.93 (s, 3H) 3.57 (s, 2H) 6.62 (br. s., 2H) 6.67 (br. s., 1H) 7.06 (d, J=8.8 Hz, 2H) 7.13 (t, J=74.12 Hz, 1H) 7.14-7.25 (m, 3H) 7.35 (s, 1H) 7.43 (d, J=8.8 Hz, 2H); MS (APPI) m/z 403 [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-5583114fcfd140a491806a659947b98f
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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