P-Anisidine → 6-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine

HRID 2239824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239824
Cl.Br[C:3]1[C:4]2[N:5]([CH:11]=[CH:12][N:13]=2)[N:6]=[C:7]([Cl:10])[C:8]=1[CH3:9].[CH3:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1.COC1C=CC(N)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[Cl:10][C:7]1[C:8]([CH3:9])=[C:3]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH3:14])=[CH:22][CH:21]=2)[C:4]2[N:5]([CH:11]=[CH:12][N:13]=2)[N:6]=1

Komponenten

7

Edukt 4

HCID 7732P-AnisidineHCID 90764-EthoxyanilineHCID 11430Potassium CarbonateHCID 866117138-bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine HCl salt

Produkt 1

HCID 866117156-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
225 °C

Versuchsvorschrift

(1d variation 1) A mixture of 8-bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine HCl salt (30 mg, 0.1 mmol) from 1c, p-methoxyaniline (20 μL, 0.15 mmol) and K2CO3 (75 mg) were suspended in NMP (600 μL) and heated in a microwave at 225° C. for 15 min. The mixture was cooled to room temperature and then treated with H2O (5 mL). The solid that precipitated out was filtered, washed with water and dried to provide 6-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine (21 mg, >90% pure by HPLC).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solid that precipitated out
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-92981fe84f5648f68fcb663cca5f5c04
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723336B2

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