Methyl iodide → HCID 46195843, compound

Participants

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 2-chloro-4-methyl-pyridin-3-ylamine (34.2 mg, 0.24 mmol, 1.2 equiv; [CAS RN 133627-45-9]), 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 rt. After 18 h, sodium hydride (13.0 mg, 0.3 mmol, 1.5 equiv; 55% free-flowing powder moistened with oil; [CAS RN 7646-69-7]) and iodomethane (56.8 mg, 25 μL, 0.4 mmol, 2.0 equiv; [CAS RN 74-88-4]) were added and stirring continued at 40° C. for 2 h. 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 2.9 mg (3%) of the title compound. MS (ISP): 424.1 [M+H]+.

Provenance & Evidence