Reaktion #6967

ord-87002b9f196d4b4bafaff983bc899b02

Reaktionsgleichung

Cl.ClCc1cnc(Nc2ccccn2)s1
(5-chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride
O=C(NC1CC1)c1ccc(F)c(O)c1
3-hydroxy-4-fluoro-N-cyclopropylbenzamide
O=S(=O)([O-])O.[K+]
KHSO4
O=C(NC1CC1)c1ccc(F)c(OCc2cnc(Nc3ccccn3)s2)c1
title compound
Ausbeute 33.0%
O=C(NC1CC1)c1ccc(F)c(OCc2cnc(Nc3ccccn3)s2)c1
N-Cyclopropyl-4-fluoro-3-[2-(pyridin-2-ylamino)-thiazol-5-ylmethoxy]-benzamide
Ausbeute 33.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONpoured onto ice
  2. 2
    Sonstigethe precipitates were collected
  3. 3
    Waschenwashed with water and ethyl acetate

Vorschrift

To a suspension of NaR (16 mg, 60% in oil) in DMF (1 mL) was added a solution of 3-hydroxy-4-fluoro-N-cyclopropylbenzamide (58.5 mg, 0.3 mmol) in DMF (1 mL) at RT. After 10 min, (5-chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride (Example 10A) (52.4 mg, 0.2 mmol) was added. The mixture was stirred at RT for 1 h and poured onto ice. The mixture was neutralized with 1 N KHSO4 solution and the precipitates were collected, washed with water and ethyl acetate to give the title compound as a light yellow solid (25.2 mg, 33%). MS m/z 385 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084160B2uspto-grants-2006_08