4-Amino-2-methylpyridine → 6-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

HRID 1943498

Reaktionsgleichung

Reaktionsgleichung von HRID 1943498
[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[N:6]([C:8]([C:11](O)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:30][C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[CH:33][N:32]=1>O=S(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[N:6]([C:8]([C:11]([NH:37][C:35]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:30])[CH:36]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 7286704-Amino-2-methylpyridineHCID 596248836-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid

Produkt 1

HCID 596246286-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid (150 mg, 0.37 mmol) in SOCl2 (2 mL) was heated at 60° C. for 1 hour. The reaction mixture was concentrated, dried under reduced pressure and dissolved in DCM (3 mL). 2-Methylpyridin-4-amine (45 mg, 0.41 mmol), and TEA (0.16 mL, 1.11 mmol) were added and the reaction mixture was stirred at room temperature for 12 hours, concentrated and then purified by silica gel chromatography (5% MeOH in DCM) to obtain 6-chloro-8-((4-methoxybenzyl)(phenyl)amino)-N-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (102 mg, 55% yield) as a yellow solid. LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA). Rt=3.263 minutes. [M+H]=499.06.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customdried under reduced pressure
  3. dissolutiondissolved in DCM (3 mL)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-e7c76ce73f8743a69e35bb53641aa026
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389527B2

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