Triethylamine → [(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456082
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.Cl.[NH2:27][NH:28][C:29]([NH2:31])=[O:30].C(N(CC)CC)C>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19](/[C:22](=[N:27]/[NH:28][C:29]([NH2:31])=[O:30])/[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 669270891-(3-((7-Fluoroquinolin-6-yl)(hydroxy)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Produkt 1

HCID 71699884[(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]ureaAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-((7-fluoroquinolin-6-yl)(hydroxy)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (100 mg, 0.27 mmol) in methanol (15 mL) was added semicarbazide hydrochloride (45 mg, 0.41 mmol). Triethyl amine was added dropwise to adjust the pH to 5-6. The reaction mixture was stirred at room temperature overnight. The precipitate was collected by filtration and dried over vacuum pump to afford 50 mg (yield: 47%) title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.68 (s, 1H), 8.89 (dd, 1H), 8.45 (d, 1H), 8.25 (m, 2H), 7.99 (d, 1H), 7.72 (d, 1H), 7.57 (s, 1H), 7.52 (q, 1H), 6.67 (b, 2H), 6.62 (s, 1H), 6.47 (b, 1H), 2.19 (s, 3H). LCMS (method A): [MH]+=394, tR=3.95 min.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. customdried over vacuum pump

Quellen und Nachweise

ORD-Eintrag
ord-bf399b70f4034a34ad6300e98ad17bc8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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