Butylamine → 2-amino-5-{3-[(butylamino)methyl]phenyl}-5-[4-(difluoro-methoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 2240975Notes

Reaction equation

HRID 2240975 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]([NH2:31])[CH2:28][CH2:29][CH3:30].[BH4-].[Na+].[OH-].[Na+]>CO>[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]([C:17]2[CH:24]=[CH:23][CH:22]=[C:19]([CH2:20][NH:31][CH2:27][CH2:28][CH2:29][CH3:30])[CH:18]=2)([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:14]([F:15])[F:16])=[CH:11][CH:12]=2)[N:6]=1

Participants

6

Reactant 4

HCID 8007ButylamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 16113437HCID 16113437, compound

Product 1

HCID 251282652-amino-5-{3-[(butylamino)methyl]phenyl}-5-[4-(difluoro-methoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-oneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A small vial (10 ml) was charged with 3-[2-Amino-4-(4-difluoromethoxy-phenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-benzaldehyde (90 mg, 250 μmol) and methanol (2 ml). To this was added butylamine (20 mg, 273 μmol). After stirring overnight at room temperature sodium borohydride (24 mg) was added, then after another 4 hours 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 78 mg (75%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.76-0.83 (m, 3H) 1.21 (quin, J=7.9 Hz, 2H) 1.31 (quin, J=6.3 Hz, 2H) 2.38 (t, J=7.0 Hz, 2H) 2.93 (s, 3H) 3.56 (s, 2H) 6.61 (br. s., 4H) 6.67 (br. s., 1H) 7.04 (d, J=8.8 Hz, 2H) 7.12 (t, J=74.18 Hz, 1H) 7.13-7.27 (m, 3H) 7.37 (s, 1H) 7.42 (d, J=8.8 Hz, 2H); MS (APPI) m/z 417 [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-54944d8e00e340458ba481394d11c0c5
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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