4-(8-methoxy-1-(1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole → 4-(8-methoxy-1-((S)-1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole

HRID 1482920Notes

Reaction equation

HRID 1482920 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])=[CH:11][C:10]2[N:9]=[CH:8][C:7]3[N:20]=[C:21]([CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[N:22]([CH:23]([CH3:27])[CH2:24][O:25][CH3:26])[C:6]=3[C:5]=2[CH:4]=1>C(O)C>[CH3:1][O:2][C:3]1[C:12]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])=[CH:11][C:10]2[N:9]=[CH:8][C:7]3[N:20]=[C:21]([CH:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)[N:22]([C@@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[C:6]=3[C:5]=2[CH:4]=1

Participants

3

Reactant 1

HCID 712589164-(8-methoxy-1-(1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole

Product 1

HCID 712590474-(8-methoxy-1-((S)-1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazoleYield 44.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(8-methoxy-1-(1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole (85 mg) was dissolved in ethanol (ca. 4 ml) with heating and sonication. Injections (400 μl) were then made via plastic syringe. The fractions between 24 min and 26.5 min were collected and the combined fraction solutions were evaporated to dryness using a rotary evaporator (30° C. bath temp). The residue was transferred to a tared glass vial using ethanol (ca 12 ml). The solvent was then removed by evaporation under a stream of nitrogen gas (room temp) to give 4-(8-methoxy-1-((S)-1-methoxypropan-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole (38 mg).

Workup

  1. temperaturewith heating
  2. customsonication
  3. customInjections (400 μl) were then made via plastic syringe
  4. customThe fractions between 24 min and 26.5 min were collected
  5. customthe combined fraction solutions were evaporated to dryness
  6. customa rotary evaporator (30° C. bath temp)
  7. customThe solvent was then removed by evaporation under a stream of nitrogen gas (room temp)

Sources & evidence

ORD record
ord-895ba27e187b4cd1814eb3b7097c4118
Source dataset
uspto-grants-2016_08
Patent number
US09416130B2

Reaction notes

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