Potassium Carbonate → 4-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine

HRID 857641

Reaktionsgleichung

Reaktionsgleichung von HRID 857641
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:22]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:28][C:24]3[C:22]4[N:23]=[C:19]([NH2:18])[S:20][C:21]=4[CH:27]=[CH:26][CH:25]=3)[CH:7]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 240572-Amino-4-hydroxybenzothiazoleHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Produkt 1

HCID 100916504-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), ((0.13 g, 0.5 mmol) and 2-amino-4-hydroxybenzothiazole (83 mg, 0.5 mmol, Astatech) in DMF (1 mL) was added potassium carbonate (0.14 g, 1 mmol) and the mixture was heated at 80° C. for 16 h with sirring. The reaction mixture was allowed to cool to room temperature and partitioned between EtOAc and brine. The layers were separated and the aq. layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated under vacuum. Purification of the residue by silica gel chromatography (2:1 hexanes:EtOAc) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 389 (M+1). Mp: 232.0–233.5° C. Anal. Calcd for C18H11F3N4OS: C, 55.67; H, 2.85; N, 14.43; S, 8.26. Found: C, 55.52; H, 3.08; N, 14.23; S, 8.36.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc and brine
  3. customThe layers were separated
  4. extractionthe aq. layer was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification of the residue by silica gel chromatography (2:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-106dcc77b787488a9421b978c6e865ee
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144888B2

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