Potassium Carbonate → HCID 25052216, Verbindung

HRID 1020268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020268
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[O:10])[S:6][CH:7]=1.[CH3:20][NH:21][C:22]1[C:27]([CH3:28])=[N:26][CH:25]=[CH:24][N:23]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:11][C:9]([NH:8][C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:21]([CH3:20])[C:22]2[C:27]([CH3:28])=[N:26][CH:25]=[CH:24][N:23]=2)[N:4]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 44327445N,3-Dimethylpyrazin-2-amineHCID 58055090HCID 58055090, Verbindung2×

Produkt 1

HCID 25052216HCID 25052216, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A CH2Cl2 (5 mL) suspension of 1-(4-(chloromethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea (Intermediate XXI) (90 mg, 0.30 mmol), N,3-dimethylpyrazin-2-amine (69 mg, 0.56 mmol) and finely powdered K2CO3 (83 mg, 0.60 mmol) was evaporated to dryness. This mix was heated at 80° C. for 60 hours. Upon cooling, the organics were taken up in CH2Cl2 (3×5 mL) and the insolubles were removed by filtration. The volatiles were then removed in vacuo. The crude product was purified with chromatography (silica 1-4% MeOH in CH2Cl2) to afford the title compound. 1H NMR (400 MHz, CDCl3): 8.00 (s, 2H), 7.23 (m, 1H), 6.95 (m, 3H), 6.60 (s, 1H), 4.45 (d, 2H), 4.37 (s, 2H), 2.87 (s, 3H), 2.52 (s, 3H). MS (ES+): M/Z 387 (M+1).

Aufarbeitung

  1. customwas evaporated to dryness
  2. temperatureUpon cooling
  3. customthe insolubles were removed by filtration
  4. customThe volatiles were then removed in vacuo
  5. customThe crude product was purified with chromatography (silica 1-4% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-59d7d571b2234a92affc9d29aee9a300
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716320B2

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