Diisopropylethylamine → [2-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(8-methoxy-3,4-dihydro-2H-quinolin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2,5-dichloro-phenoxy)-nicotinic acid (56.6 mg, 0.2 mmol, 1.0 equiv; Example 31, Step 1) in anhydrous DMF (1 mL) was added 8-methoxy-1,2,3,4-tetrahydro-quinoline (39.2 mg, 0.24 mmol, 1.2 equiv; [CAS RN 53899-17-5]), N-ethyldiisopropylamine (129.0 mg, 175 μL, 1.0 mmol, 5.0 equiv; [CAS RN 7087-68-5]) and HATU (91.2 mg, 0.24 mmol, 1.2 equiv; [CAS RN 148893-10-1]) and the reaction mixture stirred at 50° C. over night. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 10.6 mg (12%) of the title compound. MS (ISP): 429.3 [M+H]+.

Provenance & Evidence