2-Methoxyethylamine → 3-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester

HRID 474125

Reaktionsgleichung

Reaktionsgleichung von HRID 474125
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8](Cl)=[C:7]([Cl:13])[N:6]=1)=[O:4].[CH3:14][O:15][C:16]([C:18]1[C:23]([NH2:24])=[N:22][C:21](Cl)=[C:20]([Br:26])[N:19]=1)=[O:17].[CH3:27][O:28][CH2:29][CH2:30][NH2:31].CCN(CC)CC>CN(C=O)C.O>[CH3:14][O:15][C:16]([C:18]1[C:23]([NH2:24])=[N:22][C:21]([NH:6][CH2:5][CH2:3][O:2][CH3:1])=[C:20]([Br:26])[N:19]=1)=[O:17].[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH:31][CH2:30][CH2:29][O:28][CH3:27])=[C:7]([Cl:13])[N:6]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 14042144Methyl 3-amino-6-bromo-5-chloropyrazine-2-carboxylate

Produkt 2

HCID 866680893-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl esterHCID 866680903-Amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [CAS 1458-18-0] and 3-amino-6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester [CAS 14340-25-1] (799 mg, 3 mmol) in DMF was added 2-methoxy-ethylamine (0.31 ml, 3.6 mmol) and NEt3 (2.09 ml, 15 mmol) and the mixture was stirred at r.t. for 3.5 h. The reaction mixture was poured into water (150 ml) and extracted with toluene (2×150 ml). The organic layers were washed with half-saturated aq. sodium chloride, combined, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%) to provide the title compound together with 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (about 1:1) as colorless solid. This mixture was used for the next step.

Aufarbeitung

  1. extractionextracted with toluene (2×150 ml)
  2. washThe organic layers were washed with half-saturated aq. sodium chloride
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%)

Quellen und Nachweise

ORD-Eintrag
ord-ba920ba017e64817be1e45ce0ecb7fe3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637508B2

Verknüpfte Notizen

Wird geladen…