Hydrochloric Acid → HCID 66901751, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methyl-2,3-pyridinediamine (2.1 g, 17 mmol), 2-chloro-6-(trifluoromethyl)nicotinic acid (3.8 g, 17 mmol) and Cu (1 g, 17 mmol) in HOC2H5OBu was stirred at 160° C. overnight. When LCMS showed the reaction was complete, the mixture was filtered and concentrated to give a crude product, which was dissolved in THF (100 ml) in a flask equipped with a condenser and a nitrogen balloon. A solution of borane-Me2S (10 M, 10 ml, 0.1 mol) was added dropwise, and the resulting mixture was refluxed for 20 h before it was cooled, acidified to pH=1 with concentrated HCl, and refluxed for another 3 hours. The mixture was neutralized to pH=8 with saturated aqueous sodium bicarbonate, and the product was extracted with ethyl acetate (200 ml×3). The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified on silica gel eluting with pet ether:ethyl acetate (10:1) to afford the product 2-methyl-7-(trifluoromethyl)-10,11-dihydro-5H-dipyrido[2,3-b:2′,3′-e][1,4]diazepine. 1H-NMR A27111 H02393-117-1 (400 MHz, DMSO) δ 10.83 (br, 1H, NH), 7.45 (d, J=7.6 Hz, 1H, Ar—H), 7.40 (d, J=8 Hz, 1H, Ar—H), 7.16 (d, J=7.6 Hz, 1H, Ar—H), 6.61 (t, J=7.6 Hz, 1H, Ar—H), 4.23 (s, 2H, CH2), 2.51 (s, 3H, CH3).

Provenance & Evidence