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Triethylamine → 5-(2-fluorophenyl)-7-methyl-4-(1-methyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)imidazo[5,1-f][1,2,4]triazine

HRID 931341
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 931341
C(N(CC)CC)C.Br.[CH3:9][N:10]1[C:14]2[CH2:15][NH:16][CH2:17][CH2:18][C:13]=2[CH:12]=[N:11]1.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[N:27]=[C:28]([CH3:40])[N:29]2[C:34]=1[C:33](N1C=NC=N1)=[N:32][CH:31]=[N:30]2>ClCCl>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[N:27]=[C:28]([CH3:40])[N:29]2[C:34]=1[C:33]([N:16]1[CH2:17][CH2:18][C:13]3[CH:12]=[N:11][N:10]([CH3:9])[C:14]=3[CH2:15]1)=[N:32][CH:31]=[N:30]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1176784165-(2-fluorophenyl)-7-methyl-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazineHCID 1317323451-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine, hydrobromide salt

Produkt 1

HCID 917995295-(2-fluorophenyl)-7-methyl-4-(1-methyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)imidazo[5,1-f][1,2,4]triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Triethylamine (0.510 mL, 3.66 mmol) and C9 (0.333 g, 1.58 mmol) were added to a solution of C6 (0.360 g, 1.22 mmol) in dichloromethane (10 mL), and the reaction mixture was heated at 40° C. for 18 hours. The mixture was then washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification was effected first via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane), then by reversed phase HPLC (Column: Phenomenex Gemini C18, 5 μm; Mobile phase A: 0.1% ammonium hydroxide in water; Mobile phase B: 0.1% ammonium hydroxide in methanol; Gradient: 5% to 100% B). The product was obtained as a solid. Yield: 202 mg, 0.556 mmol, 46%. LCMS m/z 364.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 7.98 (s, 1H), 7.63 (ddd, J=7.6, 7.5, 1.8 Hz, 1H), 7.52 (dddd, J=8.3, 7.5, 5.2, 1.8 Hz, 1H), 7.35 (ddd, J=7.6, 7.5, 1.1 Hz, 1H), 7.22 (br ddd, J=10.0, 8.3, 1.0 Hz, 1H), 7.16 (br s, 1H), 4.45 (br s, 2H), 3.76-3.84 (m, 2H), 3.43 (s, 3H), 2.67 (s, 3H), 2.35-2.41 (m, 2H).

Aufarbeitung

  1. washThe mixture was then washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. customThe product was obtained as a solid

Quellen und Nachweise

ORD-Eintrag
ord-3c810546c4984a9c97d5b209cf468f0b
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296761B2

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