Trifluoroacetic acid → (6-(3-Methylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

HRID 1511266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511266
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[N:21][N:22]=3)[N:19]=2)[S:11][N:10]=1>C(Cl)Cl>[CH3:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH2:23][NH2:24])=[N:21][N:22]=3)[N:19]=2)[S:11][N:10]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57690989Tert-butyl (6-(3-methylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Produkt 1

HCID 57691076(6-(3-Methylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2889 μl, 37505 μmol) was added to a stirred suspension of tert-butyl (6-(3-methylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (464 mg, 1339 μmol) in DCM (10 mL) at RT. The reaction mixture was stirred at RT for 45 min. and then concentrated in vacuo. 2M NH3 in MeOH was added. Purification by MPLC (DCM/MeOH+1% NH4OH) afforded the title compound (226 mg, 69% yield). MS m/z=247.1 [M+H]+. Calc'd for C10H10N6S: 246.30.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. addition2M NH3 in MeOH was added
  3. customPurification by MPLC (DCM/MeOH+1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-c3535f31cb4b40b1b6472c82086b783a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212041B2

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