Water → 6-(6-Amino-pyrimidin-4-yloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid (4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-amide

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Reaction Conditions

Reaction Steps

A solution of 85 mg (0.35 mMol) 6-amino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine (Step 1.3) and 0.33 mMol (4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-carbamic acid phenyl ester in 2 ml DMSO is heated to 60° C. Then 65 μl (0.38 mMol) diisopropyl-ethyl-amine are added and stirring at 60° C. continued for 3 h. The resulting solution is poured into water containing 30 mg KOH and EtOAc, the aqueous layer separated off and extracted 2× with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; EtOAC→EtOAc/(EtOH+1.5% Et3N) 19:1) gives the title compound: MS: [M+1]+=513; HPLC: tARet=8.8; Anal.: C,H,N,F.

Provenance & Evidence