Phenyl 3-methylsulfonylphenylcarbamate → N-(4-(7-(Benzyloxy)-6-cyano-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)urea

HRID 853246노트

반응식

HRID 853246 반응식
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:29][S:30]([C:33]1[CH:34]=[C:35]([NH:39][C:40](=O)[O:41]C2C=CC=CC=2)[CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31]>CS(C)=O.C(OCC)(=O)C>[CH2:20]([O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:40]([NH:39][C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:34]=4)=[O:41])=[CH:28][CH:27]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[C:17]#[N:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 2

HCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 229368314-(4-Aminophenoxy)-7-(benzyloxy)-6-cyanoquinoline

생성물 1

HCID 22936455N-(4-(7-(Benzyloxy)-6-cyano-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)urea수율 100%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
85 °C

실험 절차

After dissolving 4-(4-aminophenoxy)-7-(benzyloxy)-6-cyanoquinoline (919 mg, 2.5 mmol) in dimethylsulfoxide (10 ml), phenyl N-(3-(methylsulfonyl)phenyl)carbamate (801 mg, 2.75 mmol) was added and the mixture was heated at 85° C. for 2 hours. The reaction solution was diluted with ethyl acetate and then washed with IN aqueous sodium hydroxide (10 ml), water (20 ml×2) and saturated brine (10 ml) and dried over anhydrous sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure and the residue was suspended in ethyl acetate (30 ml), after which hexane (30 ml) was added, sonication was performed and the precipitated crystals were filtered out and dried under reduced pressure to obtain the title compound (1.43 g, 2.5 mmol, quantitative) as light brown crystals.

후처리

  1. additionwas added
  2. washwashed with IN aqueous sodium hydroxide (10 ml), water (20 ml×2) and saturated brine (10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtering off the drying agent
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionafter which hexane (30 ml) was added
  7. customsonication
  8. filtrationthe precipitated crystals were filtered out
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-7be062fca3a94d3db3365e270fe386c4
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253286B2

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