Water → Benzyl 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidine-1-carboxylate

HRID 74490

Reaktionsgleichung

Reaktionsgleichung von HRID 74490
Cl[C:2]1[C:7]([N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:9]([NH2:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(O)(CC)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]=[C:9]1[NH:11][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 821241,4-Bis(diphenylphosphino)butaneHCID 516892Sodium BicarbonateHCID 46853854Benzyl 4-[1-(2-chloro-pyridin-3-yl)-ureido]-piperidine-1-carboxylate

Produkt 1

HCID 46853855Benzyl 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 64052-Methyl-2-butanolLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

1108 g (2.85 mol) benzyl 4-[1-(2-chloro-pyridin-3-yl)-ureido]-piperidine-1-carboxylate were refluxed with 720 g (8.57 mol) sodium hydrogen carbonate in 14.5 L tert-amylalcohol. 3 L of solvent were distilled off. The reaction mixture was cooled to 35° C. and mixed with 11 mL water. Then 13 g (0.058 mol) palladium acetate and 49 g (0.115 mol) 1,4-bis-(diphenylphosphino)-butane (DPPB) were added and the mixture was refluxed. It was stirred at 100° C. until the reaction was complete, cooled to RT and 7.5 L water were added. The organic phase was separated off, washed with 5 L water and then evaporated down. The oily residue was twice combined with 3 L isopropyl acetate and distilled off. Then the residue was dissolved hot in 7 L isopropyl acetate and slowly cooled to ambient temperature. The solid that crystallised out was suction filtered, washed with 2 L isopropyl acetate and tert.-butyl-methylether and dried at 50° C.

Aufarbeitung

  1. distillation3 L of solvent were distilled off
  2. additionmixed with 11 mL water
  3. temperaturethe mixture was refluxed
  4. temperaturecooled to RT
  5. customThe organic phase was separated off
  6. washwashed with 5 L water
  7. customevaporated down
  8. distillationdistilled off
  9. dissolutionThen the residue was dissolved hot in 7 L isopropyl acetate
  10. temperatureslowly cooled to ambient temperature
  11. customThe solid that crystallised out
  12. filtrationfiltered
  13. washwashed with 2 L isopropyl acetate and tert.-butyl-methylether
  14. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-b139f2a6a9814fcd9c7fa62ffd18c626
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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