Sodium Hydroxide → HCID 136009251, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (cis)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide (0.306 g, 0.571 mmol) in 1,4-dioxane (10 mL) was added aqueous NaOH (1 N, 1.50 mL, 1.50 mmol). The reaction was heated at about 50° C. for about 1 h. The layers were partitioned between DCM (25 mL) and water (10 mL). The aqueous layer was acidified with 20% aqueous citric acid to about pH 4 and extracted with DCM (4×25 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give a brown residue. The crude material was purified by flash chromatography on silica gel eluting with a gradient of 0-10% MeOH in DCM to give a racemic mixture of products as a brown residue. The compound was further purified using chiral preparative HPLC (Table 2, Method 55) to afford (3S,4R)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide (Rt=14.5 min, or =negative) (0.031 g, 14%)[Example #36]: LC/MS (Table 1, Method a) Rt=1.62 min; MS m/z: 382 (M+H)1 and (3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide (Rt=17.3 min, or =positive) (0.033 g, 15%)[Example #37]: LC/MS (Table 1, Method a) Rt=1.62 min; MS m/z: 382 (M+H)+.

Provenance & Evidence