Cyclopropanecarbonyl chloride → N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

HRID 589904

Reaktionsgleichung

Reaktionsgleichung von HRID 589904
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.C(N(CC)C(C)C)(C)C.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1>ClCCl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:24]([CH:21]3[CH2:23][CH2:22]3)=[O:25])[N:10]=2)[N:7]=1

Komponenten

5

Edukt 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Produkt 1

HCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the mixture of 6-iodo-imidazo[1,2-b]pyridazin-2-ylamine (130 mg, 0.5 mmol, 1 eq) and N,N-diisopropylethylamine (0.26 mL, 3 eq) in anhydrous dichloromethane (10 mL) at room temperature was added dropwise cyclopropane carbonyl chloride (0.26 mL, 3 eq). After the reaction mixture was stirred at ambient temperature for two hours, it was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (with 10% THF added). The organic layer was isolated, washed with brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the residue was subject to a gradient column chromatography (from DCM to MeOH-DCM 1:30) to give N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide as a white powder in amount of 51 mg.

Aufarbeitung

  1. customit was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (with 10% THF added)
  2. customThe organic layer was isolated
  3. washwashed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe upper clear solution was decanted
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d699e3077e134d508f9c2367d727eae4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233968B1

Verknüpfte Notizen

Wird geladen…