N-(3-Phenylpropyl)-1H-Imidazole-1-Carboxamide → N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea

HRID 719752Notes

Reaction equation

HRID 719752 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[NH2:5].[C:21]1([CH2:27][CH2:28][CH2:29][NH:30][C:31](N2C=CN=C2)=[O:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:21]1([CH2:27][CH2:28][CH2:29][NH:30][C:31]([NH:5][CH:4]([C:6]2[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=2)[C:3]([O:2][CH3:1])([O:19][CH3:20])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[O:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 11368189N-(3-Phenylpropyl)-1H-Imidazole-1-CarboxamideHCID 219018732,2-Dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethanamine

Product 1

HCID 21901874N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethanamine (51.12 g, 0.185 mol) and N-(3-phenylpropyl)-1H-imidazole-1-carboxamide (42.42 g, 0.185 mol) in toluene (300 mL) under N2, was stirred and heated to reflux temperature for 3 h. The solution was cooled to room temperature and the dark brown solution was diluted with ethyl acetate (200 mL). The mixture was washed with water (2×200 mL), brine (200 mL), and dried with Na2SO4. The solvents were removed in vacuo to yield a brown solid which was recrystallized from a solvent mixture of ethyl acetate/hexane (1:1) to yield an off-white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 3 h
  3. washThe mixture was washed with water (2×200 mL), brine (200 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvents were removed in vacuo
  6. customto yield a brown solid which
  7. customwas recrystallized from a solvent mixture of ethyl acetate/hexane (1:1)
  8. customto yield an off-white solid

Sources & evidence

ORD record
ord-5f9e2e5df5014217a51e2fc81406702f
Source dataset
uspto-grants-2006_11
Patent number
US07132544B2

Reaction notes

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