4-Methoxybenzylamine → HCID 178490951, Verbindung

HRID 1943456

Reaktionsgleichung

Reaktionsgleichung von HRID 1943456
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.Br[C:12]1[C:13]2[N:14]([C:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[O:23])=[CH:20][N:21]=2)[N:15]=[C:16](Cl)[CH:17]=1.ClC1C=C(Cl)C2N(C(C(NC3C=CN=CC=3)=O)=CN=2)N=1.[C@H:51]1([NH2:58])[CH2:56][CH2:55][C@H:54]([NH2:57])[CH2:53][CH2:52]1>O1CCCC1>[NH2:57][C@H:54]1[CH2:55][CH2:56][C@H:51]([NH:58][C:16]2[CH:17]=[C:12]([NH:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:13]3[N:14]([C:19]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)=[O:23])=[CH:20][N:21]=3)[N:15]=2)[CH2:52][CH2:53]1

Komponenten

6

Edukt 4

HCID 754524-MethoxybenzylamineHCID 596245908-Bromo-6-chloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideHCID 596246716,8-Dichloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideHCID 178511674HCID 178511674, Verbindung

Produkt 1

HCID 178490951HCID 178490951, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(4-methoxyphenyl)methanamine (0.050 mL, 0.383 mmol) was added to a suspension of a mixture of 8-bromo-6-chloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide and a 6,8-dichloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide 1E (0.118 g, 0.383 mmol) in tetrahydrofuran (1.0 mL) in a 2 dram screw vial equipped with a stir bar and a teflon coated screw cap. The mixture was heated at 80° C. overnight. The reaction was cooled to room temperature. The reaction was concentrated to dryness under a stream of nitrogen. (trans)-Cyclohexane-1,4-diamine (0.437 g, 3.83 mmol) was added and the mixture was heated to 160° C. After 2 h, the reaction was partitioned between dichloromethane (1.5 mL) and water (1.5 mL). The dichloromethane was removed and concentrated under a stream of nitrogen to provide 6-((trans)-4-aminocyclohexylamino)-8-(4-methoxybenzylamino)-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (0.103 g).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationThe reaction was concentrated to dryness under a stream of nitrogen
  3. temperaturethe mixture was heated to 160° C
  4. customthe reaction was partitioned between dichloromethane (1.5 mL) and water (1.5 mL)
  5. customThe dichloromethane was removed
  6. concentrationconcentrated under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-d0404cedc17145b0b2b2d7ba0d0191df
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389527B2

Verknüpfte Notizen

Wird geladen…