HCID 59380419, compound → HCID 67358116, compound

Participants

Reaction Steps

To a solution of crude material 2-(3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-benzo[4,5]thieno[2,3-d]pyrimidin-7-yloxy}-2-hydroxy-propyl)-isoindole-1,3-dione (216 mg, 0.33 mmol, from Step 1) in EtOH (5 mL) was added hydrizine (1 mL) under nitrogen. The reaction was stirred at rt for 15 h. The solvent was removed in vacuo. The crude material was purified by preparative HPLC to give 1-amino-3-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]oxy}propan-2-ol as a white solid (21 mg, 12%). 1H-NMR (CD3OD) δ 8.23 (s, 1H), 8.07 (d, J=9.2 Hz, 1H), 7.59 (d, J=2.7 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.31 (dd, J=2.7, 9.0 Hz, 1H), 7.26 (m, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.11 (d, J=9.7 Hz, 1H), 7.03 (dd, J=2.3, 9.0 Hz, 1H), 6.96 (d, J=9.2 Hz, 1H), 6.92 (td, 1H), 5.04 (s, 2H), 3.94 (m, 3H), 2.81 (m, 2H), LCMS RT=2.84 min, [M+H]+=525.1.

Provenance & Evidence