2-(Methylamino)ethanol → 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamide

HRID 551864

Reaktionsgleichung

Reaktionsgleichung von HRID 551864
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[C:5](=[O:21])[N:4]([CH3:22])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:59][NH:60][CH2:61][CH2:62][OH:63]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([N:60]([CH2:61][CH2:62][OH:63])[CH3:59])=[O:15])=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[C:5](=[O:21])[N:4]([CH3:22])[CH:3]=1

Komponenten

6

Edukt 4

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58729044HCID 58729044, Verbindung

Produkt 1

HCID 587290674-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamideAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-2-nitro-benzoic acid (3) (1.0 g, 2.72 mmol), (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate [BOP] (120 mg, 2.72 mmol,), diisopropylethylamine (1.42 mL, 8.15 mmol) and 2-methylaminoethanol (0.33 mL, 4.07 mmol) are dissolved in DMF (25 mL) at room temperature and allowed to react for 60 min. The reaction is quenched by the addition of water (120 mL) and the resulting suspension was allowed to stir for 15 min. The suspension is then filtered, washed with water (3×50 mL) and then air-dried to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamide (4) as a yellow solid (1.05 g).

Aufarbeitung

  1. customto react for 60 min
  2. customThe reaction is quenched by the addition of water (120 mL)
  3. filtrationThe suspension is then filtered
  4. washwashed with water (3×50 mL)
  5. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-ddd3e58f58504990bb68debb15943e83
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947835B2

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