Triethylamine → [3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-methyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-2-yl)-amine

HRID 2076043Notes

Reaction equation

HRID 2076043 reaction equation
CN(C)[CH:3]=[C:4]1[C:9](=O)[C:8]([CH3:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5]1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH:41][C:42]([NH2:44])=[NH:43])[CH:32]=[CH:33][C:34]=1[N:35]1[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH:41][C:42]2[N:44]=[CH:3][C:4]3[CH2:5][CH2:6][CH2:7][C:8]([CH3:17])([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:9]=3[N:43]=2)[CH:32]=[CH:33][C:34]=1[N:35]1[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 670961136-[1-Dimethylamino-methylidene]-2-methyl-2-phenylcyclohexanoneHCID 178493228HCID 178493228, compound

Product 1

HCID 57780701[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-methyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-2-yl)-amineYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-[1-dimethylamino-methylidene]-2-methyl-2-phenylcyclohexanone (103 mg, 0.42 mmol), N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (157 mg, 0.42 mmol), and triethylamine (0.29 mL, 2.1 mmol) in ethanol (1 mL) was heated at reflux for 18 h. The mixture was cooled, diluted with ethyl acetate (30 mL) and then washed with saturated aqueous sodium carbonate solution (10 mL) and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by column chromatography on silica gel using dichloromethane/methanol (20:1 v/v) as eluent to give the title compound (34 mg, 19%). MS ISP (m/e): 426.1 [(M+H)+]. mp 207-209° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureThe mixture was cooled
  4. washwashed with saturated aqueous sodium carbonate solution (10 mL) and with brine (10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residual material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2514d2d141dc403fb668673ba5b938a0
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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