Phosphorus oxychloride → HCID 86655313, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-[2-(4-methyl-piperazin-1-yl)-ethyl]-4,5-dihydro-3H-10-thia-2,3,7,9-tetraaza-cyclopenta[a]fluorene-6-ol (2 g, 5.4 mmol) in POCl3 (18 ml, 194 mmol) was heated at 105° C. (bath temperature) for 3 h. Analytical HPLC showed no more starting material and a new peak. Excess POCl3 was removed under vacuum and the residue was neutralized with 1N NaOH, extracted with CHCl3:isopropanol (v/v, 3/1). The organic phase was washed with brine, dried over Na2SO4, concentrated to afford a brown syrup, which was purified by silica gel column (CH2Cl2/2N NH3 in MeOH=100/8). The desire product was obtained as a light yellow solid (1.5 g, 71%). 1H-NMR (CD2Cl2-d2) δ 8.66 (s, 1H), 7.60 (s, 1H), 4.19 (t, 2H, J=6.2 Hz), 3.55 (t, 2H, J=8.5 Hz), 3.10 (t, 2H, J=8.3 Hz), 2.80 (t, 2H, J=6.0 Hz), 2.52-2.39 (b, 8H), 2.25 (s, 3H); LCMS RT=1.97 min; [M+H]+=389.4.

Provenance & Evidence