2,5-Dihydrofuran → HCID 67115852, compound

Participants

Reaction Conditions

Reaction Steps

A solution of PU-H71 (30 mg, 0.0585 mmol) in NMP (1.5 mL) was evacuated and back filled with nitrogen. This was repeated four times, then DIEA (15.1 mg, 21 μL, 0.117 mmol), 2,5-dihydrofuran (82 mg, 88 μL, 1.17 mmol) and Pd(PPh3)4 (13.5 mg, 0.0117 mmol) were added and the reaction mixture was heated under nitrogen at 55° C. for 20 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC two times (CH2Cl2:MeOH—NH3 (7N), 10:1, then hexane:EtOAc:CH2Cl2:MeOH—NH3 (7N), 2:1:2:0.5) to give 5.0 mg (19%) of DZ3-143. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 8.18 (s, 1H), 7.02 (s, 1H), 7.00 (s, 1H), 6.55 (m, 1H), 6.04 (s, 2H), 4.99 (m, 1H), 4.64-4.69 (m, 1H), 4.45 (m, 1H), 4.31 (t, J=6.8 Hz, 2H), 4.05 (dd, J=6.2, 9.2 Hz, 1H), 3.40 (m, 1H), 2.67 (t, J=6.4 Hz, 2H), 2.14 (m, 2H), 1.16 (d, J=6.1 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C22H27N6O3S, 455.1865; found. 455.1862; HPLC: method A Rt=6.04, method B Rt=6.32.

Provenance & Evidence