Sodium Hydroxide → HCID 118130630, compound

Participants

Reaction Conditions

Reaction Steps

To 1-(6-chlorobenzo[d]thiazol-2-yl)-3-(2-(7-hydroxy-1′-isobutyl-4-(trifluoromethyl)spiro[indoline-3,4′-piperidine]-1-yl)phenyl)urea (Example 30, 6.0 mg, 9.5 μmol) was added sodium hydroxide (95 μL, 0.095 mmol) and ammonium hydroxide (27.5 μL, 0.190 mmol). The reaction mixture was stirred at 40° C. for 18 h. The crude product was purified using a 10 minutes gradient from 0 to 100% B and pump to dryness to give the title compound Example 80 (3.5 mg, 6.0 μmol, 63% yield). 1H NMR (400 MHz, MeOD) δ ppm 1.01 (d, J=6.60 Hz, 6H), 2.12 (t, J=14.02 Hz, 3H), 2.54-2.67 (m, 1H), 2.86 (m, 1H), 2.92 (d, J=7.15 Hz, 2H), 3.01 (t, J=12.09 Hz, 1H), 3.08-3.17 (m, 1H), 3.56 (d, J=10.44 Hz, 3H), 4.20 (d, J=10.44 Hz, 1H), 6.75 (d, J=8.24 Hz, 1H), 7.03-7.14 (m, 3H), 7.16-7.26 (m, 2H), 7.30 (m, 1H), 7.59 (dd, J=8.52, 2.47 Hz, 1H), 8.10 (d, J=7.15 Hz, 1H). LCMS (ESI) m/z 587.4 (M+H)+, RT=1.69 min (Method D).

Provenance & Evidence