Triethylamine → Ethyl 4-(4-chloro-phenyl)-2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-pyrimidine-5-carboxylate

HRID 1855358Notes

Reaction equation

HRID 1855358 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([NH2:26])=[NH:25])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1.CN(C)[CH:29]=[C:30]([C:36](=O)[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[Cl:43][C:40]1[CH:39]=[CH:38][C:37]([C:36]2[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][N:26]=[C:24]([NH:23][C:13]3[CH:14]=[CH:15][C:16]([N:17]4[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]4)=[C:11]([O:10][CH3:9])[CH:12]=3)[N:25]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 54104092HCID 54104092, compoundHCID 178493228HCID 178493228, compound

Product 1

HCID 57829832Ethyl 4-(4-chloro-phenyl)-2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-pyrimidine-5-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (185 mg, 0.5 mmol), crude ethyl 3-dimethylamino-2-(4-chloro-benzoyl)-acrylate (292 mg, 1.0 mmol), and triethylamine (0.66 mL, 4.7 mmol) in ethanol (2 mL) was heated at reflux for 15 h. The mixture was cooled and diluted with ethyl acetate (50 mL). The solution was washed with sat. sodium carbonate solution (5 mL) and with brine (5 mL), dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using dichloromethane/0-20% methanol as eluent to give the title compound (157 mg, 68%) as a pale-yellow solid. Mp 216-218° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. temperatureThe mixture was cooled
  4. washThe solution was washed with sat. sodium carbonate solution (5 mL) and with brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-728591e3f99342f0851ae8652534cfa8
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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