Ethyl Acetate → HCID 86648682, compound

HRID 43733Notes

Reaction equation

HRID 43733 reaction equation
C(OCC)(=O)C.Cl.[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][NH:22][CH2:21][C@H:20]2[O:25][CH2:26][CH3:27])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15].B(F)(F)[O:29][C:30]([C:32]1[C:41](=[O:42])[C:40]2[C:35](=[C:36]([O:44][CH3:45])[C:37](F)=[CH:38][CH:39]=2)[N:34]([CH:46]2[CH2:48][CH2:47]2)[CH:33]=1)=[O:31]>CS(C)=O.C(N(CC)CC)C.O.C(O)C>[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][N:22]([C:37]3[C:36]([O:44][CH3:45])=[C:35]4[C:40]([C:41](=[O:42])[C:32]([C:30]([OH:31])=[O:29])=[CH:33][N:34]4[CH:46]4[CH2:47][CH2:48]4)=[CH:39][CH:38]=3)[CH2:21][C@H:20]2[O:25][CH2:26][CH3:27])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 57555589HCID 57555589, compoundHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648682HCID 86648682, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
40 °C

Procedure

Ethyl acetate was added to cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol), and the organic layer was washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue and (1-cyclopropyl-7-fluoro-8-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)carbonyl difluoroborate obtained in Example (146a) (82 mg, 0.30 mmol) were dissolved in DMSO (0.6 mL). Triethylamine (0.100 mL, 0.721 mmol) was added, and the mixture was stirred at 40° C. overnight. Ethanol (3 mL), water (0.3 mL) and triethylamine (0.3 mL) were added to the reaction solution, and the mixture was stirred at 80° C. for six hours. The reaction solution was cooled to room temperature. The resulting solid was collected by filtration and washed with ethanol to obtain 102.5 mg of the title compound as a pale yellow solid (62%).

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. stirringthe mixture was stirred at 80° C. for six hours
  5. temperatureThe reaction solution was cooled to room temperature
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-57e8b07dd5b743f7905e70b30732c86d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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