3,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide → {2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-{3-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-propoxy}-phenyl)-propyl]-dimethyl-ammonium bromide

HRID 882893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882893
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].[Br:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:43]=[CH:42][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:41]=[CH:40][C:33]([O:34][CH2:35][C@@H:36]([OH:39])[CH2:37][OH:38])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1>CC(=O)CC>[Br-:18].[NH2:14][C:13]1[C:8]([C:6]([NH:5][CH2:4][CH2:3][N+:2]([CH2:19][CH2:20][CH2:21][C:22]2[CH:43]=[CH:42][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:34][CH2:35][C@@H:36]([OH:39])[CH2:37][OH:38])=[CH:40][CH:41]=3)=[CH:24][CH:23]=2)([CH3:17])[CH3:1])=[O:7])=[N:9][C:10]([Cl:16])=[C:11]([NH2:15])[N:12]=1

Komponenten

4

Edukt 2

HCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2×HCID 67028182(S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol2×

Produkt 1

HCID 86656635{2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-{3-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-propoxy}-phenyl)-propyl]-dimethyl-ammonium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (0.65 g, 2.52 mmol) and (S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol (Intermediate J) (1.60 g, 3.78 mmol) in butan-2-one (25 mL) is heated at reflux overnight during which time precipitation of white solid is observed. The reaction mixture is filtered to collect the product, washed with warm acetone and dried under vacuum to afford the title compound. M+ 601. 1H NMR (400 MHz, DMSO-d6) δ 8.29 (1H, t), 7.30 (1H, br), 7.12 (2H, d), 7.11 (2H, br), 7.07 (2H, d), 6.95 (1H, br), 6.84 (2H, d), 6.82 (2H, d), 4.89 (1H, d), 4.63 (1H, t), 3.94 (1H, dd), 3.89 (2H, t), 3.81 (1H, dd), 3.77 (1H, m), 3.59 (2H, m), 3.43 (2H, m), 3.42 (2H, m), 3.34 (2H, m), 3.08 (6H, s), 2.66 (2H, m), 2.47 (2H, m), 1.96 (2H, m), 1.93 (2H, m).

Aufarbeitung

  1. temperatureat reflux overnight during which time precipitation of white solid
  2. filtrationThe reaction mixture is filtered
  3. customto collect the product
  4. washwashed with warm acetone
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bfacbfbd3feb48b7846b9390be659d88
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236808B2

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