Ethyl isocyanate → 1-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

HRID 712177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712177
[Br:1][C:2]1[C:7]2[S:8][C:9]([NH2:11])=[N:10][C:6]=2[CH:5]=[C:4]([Br:12])[N:3]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>O1CCOCC1.O>[Br:1][C:2]1[C:7]2[S:8][C:9]([NH:11][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:10][C:6]=2[CH:5]=[C:4]([Br:12])[N:3]=1

Komponenten

5

Edukt 2

HCID 8022Ethyl isocyanateHCID 580332294,6-Dibromothiazolo[5,4-c]pyridin-2-amine

Produkt 1

HCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylureaAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4,6-dibromothiazolo[5,4-c]pyridin-2-amine (1.47 g, 56.74% as per LCMS, 2.70 mmol) in 1,4-dioxane (75 mL) was added ethylisocyanate (1.30 mL, 16.25 mmol) and the resulting reaction mixture was heated to 80° C. for 16 h. The solvent was distilled off under reduced pressure and the residue was then co-distilled with hexane (twice). The solid thus obtained was stirred in hot water at 80° C. for 30 min then filtered. The solid material was purified over silica gel (100-200 M, 30-40% EtOAc-hexane) to obtain the desired product as an off-white solid (0.85 g, 82%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe solid thus obtained
  4. filtrationthen filtered
  5. customThe solid material was purified over silica gel (100-200 M, 30-40% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-811152d98b6e43118e5c05aae97a55bc
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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