Hydrochloric Acid → N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride

HRID 246665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246665
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24](COCC[Si](C)(C)C)[N:23]=[CH:22]4)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:34]>O1CCOCC1>[ClH:34].[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][N:23]=[CH:22]4)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 71280304N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Produkt 1

HCID 71280039N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochlorideAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (120 mg, 0.258 mmol) in dioxane (20 mL) was bubbled HCl gas until saturation and the reaction stirred at room temperature for 16 hours. Reaction mixture was concentrated and the residue purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions are: 40% acetonitrile/60% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min.). Concentrated HCl was added to the combined fractions containing pure product, then solvents evaporated to afford N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (20 mg, 21%) as a yellow solid. LCMS: (M+H)+=335; 1H NMR (300 MHz, CD3OD): δ 8.94 (s, 1H), 8.34 (s, 1H), 8.31 (s, 1H), 7.97 (s, 1H), 7.94 (s, 1H), 7.39 (t, 1H, J=6.9 Hz), 1.52 (s, 9H).

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customthe residue purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  4. wait40% acetonitrile/60% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min.
  5. additionConcentrated HCl was added to the combined fractions
  6. additioncontaining pure product
  7. customsolvents evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bf1c92712c134bae85e7087fec186bf8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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