Water → HCID 178434789, Verbindung

HRID 2246292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246292
[SH:1][C:2]1[NH:6][CH:5]=[N:4][N:3]=1.Cl[C:8]1[CH:9]=[CH:10][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]3[S:23][N:22]=[C:21]([CH3:24])[N:20]=3)[C:16]=2[N:17]=1.C(O[K])(C)(C)C.O>CN(C)C(=O)C>[N:4]1[N:3]=[C:2]([S:1][C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]4[S:23][N:22]=[C:21]([CH3:24])[N:20]=4)[C:16]=3[N:17]=2)[NH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 23160294(6-Chloro-pyrido[3,2-d]pyrimidin-4-yl)-3-methyl-[1,2,4]thiadiazol-5-yl-amineHCID 178418922HCID 178418922, VerbindungHCID 178527972HCID 178527972, Verbindung

Produkt 1

HCID 178434789HCID 178434789, VerbindungAusbeute 2,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Mercapto-4H-[1,2,4]triazole (54 mg; 0.54 mmol) and 100 mg (0.36 mmol) of (6-chloro-pyrido[3,2-d]pyrimidin-4-yl)-3-methyl-[1,2,4]thiadiazol-5-yl-amine were added to a solution of 80 mg (0.72 mmol) of tert-butoxy potassium in 3 ml of N,N-dimethylacetamide and the mixture was stirred at 130° C. for 16 hours. Water was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90) to give 3 mg (yield: 2%) of the title compound as a yellow solid.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90)

Quellen und Nachweise

ORD-Eintrag
ord-9e2d96fd6e9d44998cdf65a2f93b4a92
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687502B2

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