Water → HCID 23358023, compound

HRID 234539Notes

Reaction equation

HRID 234539 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][C:18]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:37]([N:39]([CH2:55][CH3:56])[C:40]([N:42]1[C:50]2[C:45](=[CH:46][C:47]([S:51](Cl)(=[O:53])=[O:52])=[CH:48][CH:49]=2)[CH2:44][CH2:43]1)=[O:41])[CH3:38].O>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][NH:16][C:17]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[N:19]([S:51]([C:47]3[CH:46]=[C:45]4[C:50](=[CH:49][CH:48]=3)[N:42]([C:40]([N:39]([CH2:55][CH3:56])[CH2:37][CH3:38])=[O:41])[CH2:43][CH2:44]4)(=[O:52])=[O:53])[C:18]2=[O:27])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19076453HCID 19076453, compoundHCID 19076580HCID 19076580, compound

Product 1

HCID 23358023HCID 23358023, compoundYield 126.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1 g of 3-[[2-(1-tert-butoxycarbonylpiperid-4-yl)ethyl]amino]-5-chloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one in 5 ml of DMF is cooled to +4° C. under an argon atmosphere and 0.087 g of sodium hydride as a 60% dispersion in oil is added. After stirring for 30 minutes at +4° C., 0.627 g of 1-(diethyl-aminocarbonyl)indoline-5-sulfonyl chloride is added and the mixture is stirred for 3 hours at RT. 50 ml of water are added to the reaction mixture, extraction is carried out with AcOEt, the organic phase is washed with a saturated solution of NaCl and with water and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (88/12; v/v) as the eluent to give 1.97 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=139° C.

Workup

  1. stirringthe mixture is stirred for 3 hours at RT
  2. washthe organic phase is washed with a saturated solution of NaCl and with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-8dd8db0623b8464bb59c7f81dd01666a
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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