Sodium Bicarbonate → 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

HRID 58106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58106
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2.C([O-])(O)=[O:24].[Na+]>C(O)(=O)C.OS(O)(=O)=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:24])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 897829316-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

Produkt 1

HCID 897832376-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

6-Methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile (0.02 g, 0.066 mmol) in acetic acid (2 mL) and H2SO4 (2 mL) was stirred at room temperature for 18 hours. The reaction mixture was subsequently poured into a conical flask containing ice and was carefully neutralized with NaHCO3 and extracted into DCM. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 45-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as white solid (0.32 g, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H), 7.42 (d, J=1.26 Hz, 1H), 7.73 (br s, 1H), 7.90-8.08 (m, 3H), 8.14 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H11F3N4O, 321.1. found 321.2.

Aufarbeitung

  1. additionThe reaction mixture was subsequently poured into a conical flask
  2. additioncontaining ice
  3. extractionextracted into DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column)
  7. washeluting with a gradient of 45-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-a57eef7e65a748dda85c07464a2797f9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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