Water → HCID 11539040, compound

HRID 1857267Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[CH:23]1([N:29]=[C:30]=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.O>C1(C)C=CC=CC=1>[CH:23]1([NH:29][C:30]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 85 °C

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (200 mg) was dissolved in toluene (5 ml) with heat, cyclohexyl isocyanate (340 mg) was added, and the admixture was stirred with heat at 80-90° C. for 30 minutes. After the addition of water, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 210 mg of the title compound (yield: 74%).

Workup

temperaturewith heat
extractionthe reaction mixture was extracted 2 times with ethyl acetate
washthe organic layer was then washed with brine
dry with materialdried with anhydrous sodium sulfate
customThe solvent was removed by reduced-pressure distillation
customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record: ord-052f74f92acd4df486623448b6cc00b4
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143764

Reaction notes

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