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

Reaction equation

HRID 1636772 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3bd3f0b56afa4ef5bbe2c30a38092e3e
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Linked notes

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