Triethylamine → HCID 178493100, compound

HRID 2076060Notes

Reaction equation

HRID 2076060 reaction equation
Cl.C(O[C:5]([CH:7]1[C:12](=O)[CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][N:9]([CH3:20])[CH2:8]1)=[O:6])C.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH:43][C:44]([NH2:46])=[NH:45])[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH:43][C:44]2[N:46]=[C:5]([OH:6])[C:7]3[CH2:8][N:9]([CH3:20])[CH2:10][CH:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:12]=3[N:45]=2)[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24200631Ethyl 1-methyl-4-oxo-5-phenylpiperidine-3-carboxylate--hydrogen chloride (1/1)HCID 178493228HCID 178493228, compound

Product 1

HCID 178493100HCID 178493100, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 1-methyl-4-oxo-5-phenyl-piperidine-3-carboxylic acid ethyl ester hydrochloride (89 mg, 0.3 mmol), N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (111 mg, 0.33 mmol), and triethylamine (0.21 mL, 1.5 mmol) in ethanol (2 mL) was heated at 78° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (40 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 ethyl acetate/0-30% ethanol as eluent to give the title compound (43 mg, 32%) as a brown solid (from ethyl acetate/cyclohexane). MS ISP (m/e): 443.5 [(M+H)+]. mp 152-155° C.

Workup

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

Sources & evidence

ORD record
ord-70dd0ff49c0d415a8f1ec38483f10bd7
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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