Diisopropylethylamine → HCID 56847658, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of A2 (50 mg, 0.16 mmol, 1.0 eq), O2 (44 mg, 0.16 mmol, 1.0 eq.) and DIPEA (62 mg, 0.48 mmol, 3.0 eq.) in dry DMF (4 mL) was added HATU (121 mg, 0.32 mmol, 2.0 eq.). The mixture was stirred for 12 h at 60° C. Then the mixture was diluted with EtOAc and washed three times with aq. NaHCO3-solution. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was purified by reverse phase RP-HPLC (column: C18), using H2O and ACN as eluents. The desired fractions were lyophilized to yield the desired compound O3 with impurities. A subsequent purification by chromatography on silica gel (DCM/MeOH=20:1) yielded the product O3 (15 mg, 0.026 mmol, 16%) as a white solid. 1H NMR (400 MHz, d6-DMSO, 300K) δ 2.34 (s, 6H), 2.72 (m, 2H), 2.98 (t, J=7.4 Hz, 2H), 3.94 (s, 6H), 6.47 (d, J=5.3 Hz, 1H), 7.40 (s, 1H), 7.44 (m, 3H), 7.53 (s, 1H), 7.77 (d, J=8.8 Hz, 1H), 8.03 (m, 3H), 8.48 (d, J=5.3 Hz, 1H), 8.51 (s, 1H), 10.44 (s, 1H). MS (ES) C31H29F2N5O4 requires: 573. Found: 574 (M+H)+.

Provenance & Evidence