5-(Chloromethyl)-1,2,3-trimethoxybenzene → HCID 178491928, Verbindung

HRID 77517

Reaktionsgleichung

Reaktionsgleichung von HRID 77517
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([NH:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=1)=[O:14])=[NH:11])[CH2:2]2.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[CH2:29]Cl>CN(C=O)C>[Cl-:23].[NH2:21][C:20]1[C:15]([C:13]([N:12]=[C:10]([NH2:11])[NH:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][C:28]4[CH:31]=[C:32]([O:36][CH3:37])[C:33]([O:34][CH3:35])=[C:26]([O:25][CH3:24])[CH:27]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:14])=[N:16][C:17]([Cl:23])=[C:18]([NH2:22])[N:19]=1

Komponenten

4

Edukt 2

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 178512394HCID 178512394, Verbindung2×

Produkt 1

HCID 178491928HCID 178491928, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine (Intermediate 4, 152 mg, content ca. 66%, 0.30 mmol) and 3,4,5-trimethoxybenzyl chloride (Aldrich, 77 mg, 0.36 mmol) is stirred in DMF (1 mL) at r.t. for ca. 18 h. The crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient). The product thus obtained is triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL), collected by filtration and dried under vacuum at 70° C. Further trituration with water (0.3 mL), filtration and drying under vacuum at 70° C. yields the title compound (35 mg).

Aufarbeitung

  1. customThe crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient)
  2. customThe product thus obtained
  3. customis triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL)
  4. filtrationcollected by filtration
  5. customdried under vacuum at 70° C
  6. filtrationFurther trituration with water (0.3 mL), filtration
  7. customdrying under vacuum at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-580fc6527acf4792bf8acfdf329ed787
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841309B2

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