Phosphorus oxychloride → HCID 71086349, compound

Temperature

106 °C

A mixture of 4,5-dihydro-1H-benzo[e][1,3]diazepin-3(2H)-one (Boyer, J. H. et al., J. Chem. Soc., Perkin Trans. I, 2137-2140 (1988)) (70 mg, 0.43 mmol) and POCl3 (805 μL, 8.63 mmol) was heated at 106° C. for 2 h. The reaction mixture was then concentrated in vacuo, dissolved in CHCl3 and azeotroped with PhMe. The residue was dissolved in THF (1.0 mL) and treated with 2-methoxy-N-methylethanamine (70 μl, 0.65 mmol). The resulting reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (29 mg, 28%). 1H NMR (CDCl3) δ 7.38-7.31 (m, 2H), 7.31-7.21 (m, 2H), 5.95 (br s, 1H), 4.61 (d, J=4.6 Hz, 2H), 4.39 (d, J=4.6 Hz, 2H), 3.56-3.51 (m, 2H), 3.42 (s, 3H), 3.40-3.36 (m, 2H), 3.10 (s, 3H); MS(ESI+) m/z 234.1 (M+H)+.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. dissolutiondissolved in CHCl3
3. customazeotroped with PhMe
4. dissolutionThe residue was dissolved in THF (1.0 mL)
5. customThe resulting reaction mixture
6. concentrationconcentrated in vacuo
7. customThe residue was purified by preparative HPLC

ORD record

ord-1f22802d31944ab8b898e5988eba0745

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346795B2