4-Methylmorpholine → 2,3-Dihydro-1-[(4'-fluoro[1,1'-biphenyl]-4-yl)sulfonyl]-(2S)-1H-indole-2-carboxylic acid methyl ester

HRID 2375763노트

반응식

HRID 2375763 반응식
[CH3:1]C(OC(=O)C1C=CC=CC=1OCCN)C.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@H:18]1[C:26]([OH:28])=[O:27].[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=2)=[CH:32][CH:31]=1.CN1CCOCC1>C(#N)C>[CH3:1][O:27][C:26]([C@@H:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]1[S:42]([C:39]1[CH:40]=[CH:41][C:36]([C:33]2[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=2)=[CH:37][CH:38]=1)(=[O:44])=[O:43])=[O:28]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2733920Indoline-2-carboxylic acid, (S)-HCID 27947494'-Fluorobiphenyl-4-sulfonyl chlorideHCID 692089562-(2-Aminoethoxy)benzoic acid 1-methylethyl ester

생성물 1

HCID 692137972,3-Dihydro-1-[(4'-fluoro[1,1'-biphenyl]-4-yl)sulfonyl]-(2S)-1H-indole-2-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 0.545 g (2.55 mmol) of the hydrochloride of the methyl ester of 2,3-dihydro-(2S)-1H-indole-2-carboxylic acid and 10 ml of acetonitrile is prepared and 0.9 g (3.32 mmol) of 4′-fluoro[1,1′-biphenyl]-4-sulfonyl chloride and 0.62 ml of N-methylmorpholine are added. The reaction mixture is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and washed with 3 times 75 ml of water. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure. The crude product is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (98/2; v/v) as the eluent to give 0.83 g of the expected compound in the form of a white solid (yield=79%).

후처리

  1. customis prepared
  2. concentrationconcentrated under reduced pressure
  3. washwashed with 3 times 75 ml of water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (98/2; v/v) as the eluent

출처 및 근거

ORD 기록
ord-f2a6d25bf8bd4d76b475a127cb41f42c
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465811B2

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