Hydrochloric Acid → 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

HRID 1183022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183022
C(OC(=O)[NH:7][C@H:8]([CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15])[CH2:9][CH2:10][CH3:11])(C)(C)C.Cl>O1CCOCC1>[ClH:24].[NH2:7][C@@H:8]([CH2:9][CH2:10][CH3:11])[CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86651887((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of ((S)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester (1.30 g, 3.49 mmol) in 1,4-dioxane (20 mL) is added HCl (50 mL of a 4 M solution in 1,4-dioxane, 200 mmol) and the reaction mixture is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the yellow solid obtained is triturated with diethyl ether; the diethyl ether layer is decanted and the product is dissolved in a minimal volume of MeOH and is precipitated by the addition of diethyl ether. The solvent is decanted and the resulting solid is dried under vacuum to afford the title compound. [M+H]+ 233. 1H NMR (400 MHz, CDCl3) δ 8.16 (1H, t), 7.89 (2H, br), 7.07 (4H, br), 3.42-3.38 (2H, m), 3.27-3.18 (1H, m), 1.54-1.47 (2H, m), 1.44-1.35 (2H, m), 0.89 (3H, t).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe yellow solid obtained
  3. customis triturated with diethyl ether
  4. customthe diethyl ether layer is decanted
  5. dissolutionthe product is dissolved in a minimal volume of MeOH
  6. customis precipitated by the addition of diethyl ether
  7. customThe solvent is decanted
  8. customthe resulting solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3aa6ae72904c4631b107490ae524f89d
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664228B2

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