Sodium Hydroxide → HCID 24986678, compound

Participants

Reaction Steps

N-Benzene sulfonyl-5,6,7,8-tetrahydro-7,7-dimethyl-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiazolo[5,4-c]azepin-4-one (Made using methods D and E) (79 mg, 1.0 Eq.) was suspended/dissolved in EtOH (4.5 mL)and NaOH (15 wt %, 0.5 mL, ≈11 Eq.) was added. The reaction mixture was refluxed for 4 hours. The reaction mixture was then allowed to cool to RT, and the solvent removed in vacuo. The mixture was partitioned between EtOAc/sat. aq. NH4Cl, and extracted into EtOAc (3×20 mL). The combined organic layers were washed with 15 wt % NaOH (1×10 mL), brine (1×10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (5% MeOH/95% DCM), followed by tritration in Et2O. The precipitate was then washed with pentane. The title compound was obtained as a tangerine solid (27.8 mg, 52% yield); 1H NMR (DMSO D6) 1.1(6H, s), 3.0(4H, m), 7.0(1H, m), 7.6(1H, m), 7.7(1H, m), 8.3(2H, m), 12.1(1H, br s); LC/MS M+1 (obs.) 313.20; LC/MS M−1 (obs.) 311.40.

Provenance & Evidence