Water → HCID 59300520, compound

Participants

Reaction Steps

To a solution of ethyl ((1S)-5-{3-[[4-(1,3-benzodioxol-5-yl)-2-pyrimidinyl](methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 292, 35 mg, 0.071 mmol) in THF (2 mL), ethanol (1 mL), and water (2 mL) was added LiOH.H2O (7 mg, 0.29 mmol), and the mixture was stirred at rt for 16 h. The reaction mixture was then extracted with Et2O (2×), organic layers discarded, and the remaining aqueous solution was acidified to pH ˜5 using HCl (1 M aqueous solution). The aqueous solution was then extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to give 9 mg (27%) of the product. 1H NMR (400 MHz, CDCl3): δ 1.70-1.80 (m, 1H), 2.15-2.20 (m, 2H), 2.32-2.50 (m, 2H), 2.71 (dd, 1H), 2.83-2.95 (m, 2H), 3.30 (s, 3H), 3.51-3.64 (m, 1H), 3.72 (q, 2H), 3.99 (t, 2H), 6.00 (s, 2H), 6.62 (d, 1H), 6.54 (s, 1H), 6.80 (d, 2H), 7.05 (d, 1H), 7.61 (s, 2H), 8.30 (d, 1H); LC-MS: RT=2.50 min, (M+H)+ 462.3.

Provenance & Evidence