C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1.O.CO>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:7]1[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[N:9][C:8]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1To a solution of 6-(2-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid methyl ester (0.15 g) in tetrahydrofuran (2 mL), water (0.5 mL) and methanol (0.5 mL) was added at room temperature 1 ml of a 1M solution of lithium hydroxide in water and the mixture was stirred for 2 h. The resulting solution was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic layer was washed with water and brine. The organic phase was dried over magnesium sulfate and evaporated to yield 0.14 g of the title compound as white solid, MS (ISP) 304.1 (M+H)+.
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