Hydrochloric Acid → HCID 86609857、化合物

HRID 245006ノート

反応式

HRID 245006 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 86609857HCID 86609857、化合物収率 56%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3cfcdb6c5f5496b85bb5d8d99263e3f
出典データセット
uspto-grants-2014_02
特許番号
US08658681B2

反応ノート

読み込み中…