Trifluoroacetic acid → 2-(2,6-Dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-ylamine

HRID 626748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626748
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[C:20]2=[CH:21][N:22]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:23]=[C:19]2[C:18]([F:32])=[CH:17][N:16]=1)(C)(C)C>C(Cl)Cl>[Cl:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([Cl:30])[C:24]=1[N:22]1[CH:21]=[C:20]2[C:15]([NH2:14])=[N:16][CH:17]=[C:18]([F:32])[C:19]2=[N:23]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 69674902[2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 696713582-(2,6-Dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-ylamineAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (2.0 ml) was added to a mixture of [2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester (390 mg, 1 mmol) in DCM (5 mL) and the reaction mixture was stirred at room temperature for 3.5 h. The volatiles were removed under reduced pressure and the resultant residue was dissolved in DCM and washed with saturated aqueous sodium bicarbonate solution (×2) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid (226 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.74 (d, J=3.0 Hz, 1H), 7.82-7.78 (m, 2H), 7.72-7.68 (m, 1H), 7.53 (d, J=4.3 Hz, 1H), 6.86 (br s, 2H).

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe resultant residue was dissolved in DCM
  3. washwashed with saturated aqueous sodium bicarbonate solution (×2) and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f026c94abade42ffabc22e7e6d43a918
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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