Triethylamine → HCID 23153909, compound

HRID 1175798Notes

Reaction equation

HRID 1175798 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:32]([NH:33][C:34](=[O:36])[CH3:35])=[C:13]3[C:14](=[O:31])[N:15]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[N:11]2)=[CH:6][CH:5]=1.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.[CH3:44]S(Cl)(=O)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:12]3=[N:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][N:39]5[CH2:40][CH2:41][CH2:44][CH2:43][CH2:42]5)=[CH:9][CH:8]=4)[C:32]([NH:33][C:34](=[O:36])[CH3:35])=[C:13]3[C:14]2=[O:31])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 23154093HCID 23154093, compound

Product 1

HCID 23153909HCID 23153909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-{2-[4-(2-hydroxyethyl)phenyl]-5-(4-methoxybenzyl)-4-oxo-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-3-yl}acetamide (0.2 g) and triethylamine (0.12 ml) in tetrahydrofuran (25 ml) was added dropwise methanesulfonyl chloride (0.048 ml) at 0° C. The solution was stirred at 0° C. for 2 hours and at room temperature for 15 minutes, an aqueous sodium hydrogen carbonate solution was added thereto, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. To the residue was added ethanol (30 ml), triethylamine (0.087 ml), piperidine (0.045 ml) and the mixture was refluxed with heating. After 2 hours, piperidine (0.1 ml) was added thereto, and the mixture was stirred with heating for 6 hours. The solvent was distilled off under reduced pressure, ethyl acetate was added thereto, and extracted with 1N hydrochloric acid. The aqueous layer was washed ether, basified by adding a 2N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated under reduced pressure to obtain the target compound (0.13 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added ethanol (30 ml), triethylamine (0.087 ml), piperidine (0.045 ml)
  6. temperaturethe mixture was refluxed
  7. temperaturewith heating
  8. waitAfter 2 hours
  9. additionpiperidine (0.1 ml) was added
  10. stirringthe mixture was stirred
  11. temperaturewith heating for 6 hours
  12. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  13. additionwas added
  14. extractionextracted with 1N hydrochloric acid
  15. washThe aqueous layer was washed ether
  16. additionby adding a 2N aqueous sodium hydroxide solution
  17. extractionextracted with ethyl acetate
  18. washThe extract was washed with saturated brine
  19. customdried
  20. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af19d5c5cb5b42c5ad5d125c7600a143
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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