Hydrochloric Acid → HCID 86609857, 화합물

HRID 1927355노트

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HRID 1927355 반응식
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[S:3].[C:16]([C:18]1([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=O)=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19]1)#N.[CH3:33][OH:34].Cl.CN(C=[O:40])C>CC(C)=O.ClCCl.O>[CH3:33][O:34][C:30](=[O:32])[CH2:29][C:26]1[CH:27]=[CH:28][C:23]([N:22]2[C:2](=[S:3])[N:1]([C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=3)[C:16](=[O:40])[C:18]32[CH2:21][CH2:20][CH2:19]3)=[CH:24][CH:25]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6228DimethylformamideHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 67132001[4-(1-Cyanocyclobutylamino)phenyl]acetic acid

생성물 1

HCID 86609857HCID 86609857, 화합물수율 56%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-isothiocyanato-2-trifluoromethylbenzonitrile (1a) (0.638 g, 2.8 mmol) and [4-(1-cyanocyclobutylamino)phenyl]acetic acid (46a) (0.46 g, 2.0 mmol) in DMF (5 ml) was stirred at room temperature for 15 hours. To this mixture were added methanol (20 ml) and aq. 2N HCl (10 ml). The second mixture was refluxed for 1 h. After being cooled to room temperature, the reaction mixture was poured into cold water (10 ml) and extracted with ethyl acetate (3×50 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane pure and then dichloromethane:acetone, 95:5) to yield {4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}acetic acid methyl ester (46b) [RD146] (0.532 g, 1.124 mmol, 56%), the structure of which is illustrated in Formula 15, as a white powder.

후처리

  1. temperatureThe second mixture was refluxed for 1 h
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane pure

출처 및 근거

ORD 기록
ord-170403e61cec41c4b8211e9da837cd0c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183274B2

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