Reaktion #422264

Reaktionsgleichung

ammonium chloride

KOtBu

methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

HCl

2-(Bromomethyl)pyridine hydrobromide

→

N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochloride

Ausbeute 60.5%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 30 minutes
2. 2
   Extraktionthe reaction mixture was extracted with EtOAc
3. 3
   SonstigeThe concentrated residue was purified on silica gel

Vorschrift

A 20 mL vial was charged with methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (135.8 mg, 0.338 mmol) and THF (0.5 mL). 1M KOtBu in THF (1.184 mL, 1.184 mmol) was added and the reaction mixture was stirred at room temperature for 30 seconds. 2-(Bromomethyl)pyridine hydrobromide (85.55 mg, 0.3382 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride was added and the reaction mixture was extracted with EtOAc. The concentrated residue was purified on silica gel to afford N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochloride (98.2 mg, 60.5% yield) as a pale yellow solid after HCl salt formation. 1H NMR (d6-DMSO) δ 8.66 (dd, 1H), 8.22 (td, 1H), 8.12 (d, 1H), 7.70 (t, 1H), 7.62 (d, 1H), 7.45 (m, 2H), 7.23 (t, 1H), 7.16 (d, 1H), 7.06 (m, 2H), 6.82 (m, 1H), 4.42 (s, 2H), 2.29 (s, 3H); Mass spectrum (esi) m/z=407.2 (100) (M+H-2HCl).

Quelle