Hydrochloric Acid → 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid

HRID 1959371

Reaktionsgleichung

Reaktionsgleichung von HRID 1959371
[NH2:1][C:2]1[C:3]([C:19]([O:21]C)=[O:20])=[N:4][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:6][N:7]=1.[OH-].[Na+].Cl>CO.O>[NH2:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[N:4][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH:9]=2)=[CH:6][N:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66745419methyl 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylate

Produkt 1

HCID 667448673-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acidAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of methyl 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylate (5.5 g, 16.85 mmol) in MeOH (30 mL) was treated with a solution of NaOH (8.425 mL of 2 M, 16.85 mmol) in H2O (30 mL). The resulting mixture was heated to 60° C. for 2 hours. After this time the solution was allowed to cool, neutralised with HCl and the resultant precipitate filtered (3.6 g, 65% Yield). 1H NMR (400.0 MHz, DMSO) d 1.20 (3H, t), 2.65 (2H, br s), 3.11 (2H, q), 3.44 (2H, m), 3.94 (2H, m), 6.60 (1H, m), 7.51 (2H, br s), 7.95 (1H, s), 8.52 (1H, s) ppm; MS (ES+) 312.97

Aufarbeitung

  1. temperatureto cool
  2. filtrationthe resultant precipitate filtered (3.6 g, 65% Yield)

Quellen und Nachweise

ORD-Eintrag
ord-d5ac50a1a4e24607b7a15a2cf44d29d4
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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