Sodium Bicarbonate → HCID 66744433, Verbindung

HRID 1959394

Reaktionsgleichung

Reaktionsgleichung von HRID 1959394
[NH2:1][C:2]1[C:3]([C:19]([NH:21][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[O:20])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH2:17]([S:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:4]=[C:3]([C:19]3[O:20][C:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:22][N:21]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:13][CH2:12]1)(=[O:15])=[O:16])[CH3:18]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 667454513-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide

Produkt 1

HCID 66744433HCID 66744433, VerbindungAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

3-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide (80 mg, 0.1850 mmol) in H2SO4 (1.5 mL) was stirred at ambient temperature for 16 hours. The reaction was neutralised by addition of NaHCO3 solution and then extracted with EtOAc (3×), combined organics dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as an orange solid (4.5 mg, 6% Yield). 1H NMR (DMSO) d 1.25 (3H, t), 3.11 (2H, q), 3.35 masked signal, 3.54 (4H, m), 7.00 (2H, br s), 7.42 (1H, m), 7.53 (2H, m), 7.84 (2H, m), 7.99 (1H, s), 8.14 (1H, s) ppm; MS (ES+) 415.0

Aufarbeitung

  1. extractionextracted with EtOAc (3×)
  2. dry with materialcombined organics dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  5. customThe fractions were collected
  6. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-c523891bce054fcdab0d1a0484ae5983
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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