Formaldehyde → (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Participants

Reaction Steps

To a solution of (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride (110 mg, 0.27 mmol)) in a 1:1 mixture of MeOH/THF (3 mL) was added paraformaldehyde (7.5 mg, 0.24 mmol) followed by NaCNBH3 (70 mg 1.2 mmol) and stirred at rt for 16 h. The reaction mixture was quenched by the addition of 2 N NaHCO3 (1 mL), eluted through an SCX ion-exchange column and converted to HCl salt using General Procedure D-2 (Scheme II) to obtain the desired product (67 mg, 60%) as a white solid: ESI MS m/z 425 [C24H25FN2O2S+H]+;

Provenance & Evidence