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

HRID 1043013Notes

Reaction equation

HRID 1043013 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]=1

Participants

3

Reactant 1

HCID 529342747-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 529342757-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1S)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. customThe solutions were purified by chiral HPLC
  2. washonto a Chiralpak IA column (20 um, 5 cm×25 cm) and elution with ethanol/heptanes (30%, flow rate 50 ml/min, wavelength 215 nm)

Sources & evidence

ORD record
ord-936cc96691304eb28e4f9c49656fd8f1
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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