N-Methylpiperidine → 2,2,2-trichloroethyl N-[3-[[(3S)-3-[(4,6-dichloro-1-benzothiophen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidoyl]carbamate

HRID 1636772

반응식

HRID 1636772 반응식
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:17]2[CH:16]=[C:15]([S:18]([NH:21][C@H:22]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=4)[C:31]([NH2:33])=[NH:32])[C:23]3=[O:37])(=[O:20])=[O:19])[S:14][C:13]=2[CH:12]=[C:11]([Cl:38])[CH:10]=1.CN1CCCCC1.Cl[C:47]([O:49][CH2:50][C:51]([Cl:54])([Cl:53])[Cl:52])=[O:48]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[Cl:52][C:51]([Cl:54])([Cl:53])[CH2:50][O:49][C:47](=[O:48])[NH:32][C:31]([C:30]1[CH:34]=[CH:35][CH:36]=[C:28]([CH2:27][N:24]2[CH2:25][CH2:26][C@H:22]([NH:21][S:18]([C:15]3[S:14][C:13]4[CH:12]=[C:11]([Cl:38])[CH:10]=[C:9]([Cl:8])[C:17]=4[CH:16]=3)(=[O:19])=[O:20])[C:23]2=[O:37])[CH:29]=1)=[NH:33]

참가 물질

6

반응물 3

HCID 12291N-MethylpiperidineHCID 870632,2,2-Trichloroethyl chloroformateHCID 228835403-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate

생성물 1

HCID 1398310982,2,2-trichloroethyl N-[3-[[(3S)-3-[(4,6-dichloro-1-benzothiophen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidoyl]carbamate수율 75%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a solution of 3-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluroacetate (0.25 g, 0.40 mmol), prepared as in EXAMPLE 14, Part E, in 4 mL of CH2Cl2 :DMF (10:1) is added N-methyl piperidine (0.12 g, 1.2 mmol) followed by trichloroethyl chloroformate (0.93 g, 0.44 mmol). The solution is stirred for 16 hours. After this time, the solution is diluted with EtOAc. The organic layer is washed with 1N HCl, H2O, saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (0.20 g, 0.30 mmol) as a white solid.

후처리

  1. washThe organic layer is washed with 1N HCl, H2O, saturated NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography
  6. washeluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-3bd3f0b56afa4ef5bbe2c30a38092e3e
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06034093

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