Ethylmorpholine → 4-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

HRID 1185560노트

반응식

HRID 1185560 반응식
[C:1]([C@H:4]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=1)[CH3:5])([OH:3])=O.F[C:22]1C(O)=C(F)C(F)=C(F)C=1F.Cl.[CH:34]1([NH:38][C:39]([C@@H:41]2[CH2:45][CH2:44][CH2:43][NH:42]2)=[O:40])[CH2:37][CH2:36][CH2:35]1.C(N1CCOCC1)C>C(Cl)Cl.O.C(Cl)CCl>[CH3:22][O:20][C:18]([C:9]1[CH:8]=[C:7]([O:6][C@H:4]([CH3:5])[C:1]([N:42]2[CH2:43][CH2:44][CH2:45][C@H:41]2[C:39](=[O:40])[NH:38][CH:34]2[CH2:37][CH2:36][CH2:35]2)=[O:3])[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[N:10]=1)=[O:19]

참가 물질

8

반응물 4

HCID 7525EthylmorpholineHCID 13041PentafluorophenolHCID 68597555(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochlorideHCID 68598842HCID 68598842, 화합물

생성물 1

HCID 686020364-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 1.30 g 4-((R)-1-Carboxy-ethoxy)-7-methyl-quinoline-2-carboxylic acid in 10 ml DCM, 1.24 g pentafluorophenol and 1.29 g EDC were added. The mixture was stirred under exclusion of moisture until LCMS indicated complete conversion to the corresponding pentafluorophenolester. (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochloride (1.10 g) was mixed with 1.1 ml N-ethylmorpholine and 5 ml DCM and this mixture added dropwise to the solution of the pentafluorophenolester. After 12 h the reaction mixture was diluted with water and extracted with DCM. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica eluting with ethyl acetate/heptane gradient. Yield: 1.40 g.

후처리

  1. additionthis mixture added dropwise to the solution of the pentafluorophenolester
  2. extractionextracted with DCM

출처 및 근거

ORD 기록
ord-41f7b184e12b413188878ca786c33331
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669266B2

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