1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-chloro-3-trifluoromethyl-phenyl)-3-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-urea

HRID 38076

Reaktionsgleichung

Reaktionsgleichung von HRID 38076
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)=[N:9][N:10]3[CH2:15][CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:8]3[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[C:11]4[S:12][CH2:13][CH2:14][CH2:15][N:10]4[N:9]=3)[CH:17]=2)=[O:32])=[CH:26][C:25]=1[C:33]([F:34])([F:35])[F:36]

Komponenten

4

Edukt 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 674228643-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine

Produkt 1

HCID 584770911-(4-chloro-3-trifluoromethyl-phenyl)-3-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-ureaAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine (50 mg, 0.162 mmol) was dissolved in dry DCM under nitrogen atmosphere. 4-chloro-3-trifluoromethylphenylisocyanate (43 mg, 0.195 mmol, 1.2 eq) was added, the mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The crude product was purified by silica gel chromatography (eluant: 100% ethyl acetate) to give 64 mg (75%) of 1-(4-chloro-3-trifluoromethyl-phenyl)-3-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-urea as white powder.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by silica gel chromatography (eluant: 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d8e75fc0e10f44a69b562d301deb0c06
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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