Trifluoroacetic acid → HCID 178457117, Verbindung

HRID 711306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711306
[CH3:1][CH:2]([NH:4][CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8](C(OC(C)(C)C)=O)[N:7]=1)[CH3:3].[F:22][C:23]([F:35])([F:34])[S:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:3][CH:2]([N:4]([CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1)[C:32]([NH:31][C:28]1[CH:29]=[CH:30][C:25]([S:24][C:23]([F:34])([F:22])[F:35])=[CH:26][CH:27]=1)=[O:33])[CH3:1]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 90023206HCID 90023206, Verbindung

Produkt 1

HCID 178457117HCID 178457117, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To crude tert-butyl 3-[(propan-2-ylamino)methyl]-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (75 mg, 0.26 mmol) in 2 mL CH2Cl2 was added 4-(trifluoromethylthio) phenylisocyanate (57 mg, 0.26 mmol). The reaction was allowed to stir at ambient temperature for 16 h. To the reaction solution was added trifluoroacetic acid (1.0 mL, 1.35 mmol). The solution was allowed to stir at ambient temperature for 1 h, concentrated, and purified on a Gilson reverse phase preparatory instrument. The aqueous fractions were partitioned between saturated Na2CO3 and ethylacetate. The organics were washed with water and brine, dried over Na2CO3, filtered, and purified by silica gel chromatography to give 1-(1-methylethyl)-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-3-{4-[(trifluoromethyl)sulfanyl]phenyl}urea. 1H NMR (400 MHz, CDCl3): δ 11.69 (s, 1 H); 8.62 (dd, J=4.6, 1.5 Hz, 1 H); 8.54 (s, 1 H); 8.22 (dd, J=8.1, 1.5 Hz, 1 H); 7.51 (d, J=3.1 Hz, 4H); 7.24-7.21 (m, 1 H); 4.71 (s, 2 H); 4.61-4.51 (m, 1 H); 1.24 (d, J=6.8 Hz, 6 H. LCMS [M+H]+=410.1.

Aufarbeitung

  1. stirringto stir at ambient temperature for 1 h
  2. concentrationconcentrated
  3. custompurified on a Gilson reverse phase preparatory instrument
  4. customThe aqueous fractions were partitioned between saturated Na2CO3 and ethylacetate
  5. washThe organics were washed with water and brine
  6. dry with materialdried over Na2CO3
  7. filtrationfiltered
  8. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1b6284b96040481586facdfee5526315
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181261B2

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