Hydrochloric Acid → HCID 86609864, 화합물

HRID 2273928노트

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HRID 2273928 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:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19]1)#N.[CH3:32][OH:33].Cl.CN(C=[O:39])C>O>[CH3:32][O:33][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][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:39])[C:18]32[CH2:21][CH2:20][CH2:19]3)=[CH:24][CH:25]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6228DimethylformamideHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 671321724-(1-Cyanocyclobutylamino)benzoic acid

생성물 1

HCID 86609864HCID 86609864, 화합물수율 12%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

A mixture of 4-isothiocyanato-2-trifluoromethylbenzonitrile (1a) (0.51 g, 2.22 mmol) and 4-(1-cyanocyclobutylamino)benzoic acid (51a) (0.343 g, 1.59 mmol) in DMF (2 ml) was heated under microwave irradiation at 60° C. and stirred for 16 hours. To this mixture were added methanol (10 ml) and aq. 2M HCl (5 ml). The second mixture was refluxed for 12 hours. After being cooled to room temperature, the reaction mixture was poured into cold water (20 ml) and extracted with ethyl acetate (3×30 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane:acetone, 95:5) to yield 4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-benzoic acid methyl ester (51b) [RD159] (0.09 g, 0.196 mmol, 12%), the structure of which is illustrated in Formula 25, as a white powder and N-(3-cyano-4-trifluoromethylphenyl)-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]benzamide (51b′) [RD160] (0.28 g, 0.45 mmol, 29%), the structure of which is illustrated in Formula 26, as a white powder.

후처리

  1. temperatureThe second mixture was refluxed for 12 hours
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane:acetone, 95:5)

출처 및 근거

ORD 기록
ord-e56eace645854b5a81fc3c073af6478a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126941B2

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