7-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one → 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1S)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one
Reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([CH:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH3:21])[C:18](=[O:28])[NH:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([C@H:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH3:21])[C:18](=[O:28])[NH:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
7-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (for a preparation see Example 38, ˜50 mg) was dissolved in 3 ml of ethanol (3 ml) and heptanes (3 ml) with warming (×3). The solutions were purified by chiral HPLC using 6× injection (3 ml) of the above solution onto a Chiralpak IA column (20 um, 5 cm×25 cm) and elution with ethanol/heptanes (30%, flow rate 50 ml/min, wavelength 215 nm). The mixed fractions were reduced to dryness in vacuo and reprocessed as described in the method above. The bulked fractions of the first eluting enantiomer were reduced to dryness in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1S)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (61 mg).