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Hydrochloric Acid → 2-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrile

HRID 910891
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 910891
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.F[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C1COCC1.CCOCC>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 678552-FluorobenzonitrileHCID 178431958HCID 178431958, Verbindung

Produkt 1

HCID 166781042-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrileAusbeute 8,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel2×
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-(4-Methylthiazol-2-ylamino)pyridin-4-ol (0.100 g, 0.483 mmol), 2-fluorobenzonitrile (0.064 g, 0.531-mmol) and potassium carbonate (0.167 g, 1.21 mmol) were combined in DMSO and heated at 90° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was purified by MPLC, eluting with 3:1 hexane:ethyl acetate to afford the free base. The free base was dissolved in THF (3 mL) and 1M HCl in ether (6 mL) was added. The solution was diluted with ether (15 mL), triturated for 10 minutes, and filtered to afford 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrile (0.013 g, 8.65% yield) as white solid. 1H NMR (CDCl3) δ 8.26 (d, 1H), 7.72 (dd, 1H), 7.60 (m, 1H), 7.32 (dt, 1H), 7.14 (d, 1H), 6.53 (dd, 1H), 6.42 (d, 1H), 6.33 (d, 1H), 2.23 (d, 3H); HPLC Rt=2.67 min; Mass spectrum (esi) m/z=309 (M+H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by MPLC
  6. washeluting with 3:1 hexane
  7. customethyl acetate to afford the free base
  8. customtriturated for 10 minutes
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-ac89c7fcb86b4bd2af59eaa0083cf9b6
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022222B2

Notizen zur Reaktion

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