Tetrahydrofuran → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide p-toluenesulfonate

HRID 1667970

Reaktionsgleichung

Reaktionsgleichung von HRID 1667970
[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([F:32])=[C:20]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:21]=4)=[N:11][N:10]3[CH:33]=2)=[O:5])[CH2:3][CH2:2]1.O1CCCC1.O.[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:42][CH:41]=1>C(O)C>[C:40]1([CH3:50])[CH:41]=[CH:42][C:43]([S:46]([OH:49])(=[O:47])=[O:48])=[CH:44][CH:45]=1.[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([F:32])=[C:20]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:21]=4)=[N:11][N:10]3[CH:33]=2)=[O:5])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 24767979N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

Produkt 1

HCID 86630645N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide p-toluenesulfonateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (225 mg, 0.5 mmol) were added tetrahydrofuran (5.0 mL) and ethanol (5.0 mL), dissolved at 70° C., and p-toluenesulfonic acid monohydrate (95 mg, 0.5 mmol) was added thereto. Ethanol (15.0 mL) was further added to the mixture and insoluble material was filtered off. The filtrate was concentrated, ethyl acetate (10 mL) and ethanol (10 mL) were added thereto, and the mixture was concentrated again. Ethyl acetate (10 mL) and ethanol (1.0 mL) were added thereto, and the mixture was stood at room temperature for 6 hr. The precipitated crystals were collected by filtration, washed successively with a small amount of ethanol and diethyl ether, and dried under reduced pressure at 80° C. for 6 hr to give the title compound (285 mg, 92%) as white crystals.

Aufarbeitung

  1. dissolutiondissolved at 70° C.
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated
  4. additionethyl acetate (10 mL) and ethanol (10 mL) were added
  5. concentrationthe mixture was concentrated again
  6. additionEthyl acetate (10 mL) and ethanol (1.0 mL) were added
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed successively with a small amount of ethanol and diethyl ether
  9. customdried under reduced pressure at 80° C. for 6 hr

Quellen und Nachweise

ORD-Eintrag
ord-325601b38528456d9172dea8da8dd72d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044049B2

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