Benzyl isocyanate → 3-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamide

HRID 646690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646690
[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:6][N:7]=1.[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:27]([NH:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:28])[CH:9]=2)=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 76639Benzyl isocyanateHCID 100374223-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide

Produkt 1

HCID 686505323-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide (0.25 g, 1.03 mmol) in dry tetrahydrofuran (2 mL) was added benzyl isocyanate (0.15 g, 1.12 mmol). The mixture was allowed to stir overnight. The solid product was filtered from the reaction mixture and triturated with hexane/ethyl acetate (9:1). The solid was collected by filtration and dried to afford 3-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamide (0.26 g, 70% yield) as light yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.80 (m, 1H), 8.64 (s, 1H), 8.02 (s, 1H), 7.68 (d, 1H), 7.58 (d, 1H), 7.30 (m, 8H), 4.30 (d, 2H), 2.80 (d, 3H); MS (EI) for C20H20N6O2: 377 (MH+).

Aufarbeitung

  1. filtrationThe solid product was filtered from the reaction mixture
  2. customtriturated with hexane/ethyl acetate (9:1)
  3. filtrationThe solid was collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4df6275a81374b0e81473cf4e392ca3d
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704995B2

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