Pyrrolidine → HCID 54143732, compound

HRID 1837387Notes

Reaction equation

HRID 1837387 reaction equation
[CH:1]1([C@@H:7]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:35](=[N:38][S:39]([CH3:42])(=[O:41])=[O:40])SC)[CH2:31][CH2:30]2)=[O:11])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1>>[CH:1]1([C@@H:7]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[CH2:28][N:29]2[CH2:30][CH2:31][N:32]([C:35](=[N:38][S:39]([CH3:42])(=[O:41])=[O:40])[N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)[CH2:33][CH2:34]2)=[O:11])[CH3:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 54563129HCID 54563129, compound

Product 1

HCID 54143732HCID 54143732, compoundYield 65%

Procedure

0.46 g (0.76 mmol) of crude 3-[4-(1-methanesulfonylimino-1-methylsulfanyl-methyl)-piperazin-1-ylmethyl]-2-phenyl-quinoline-4-carboxylic acid ((S)-1-cyclohexyl-ethyl)-amide (compound of Description 16) and 5 ml of pyrrolidine were heated to reflux for 5 h. The excess of pyrrolidine was removed in vacuo and the residue was purified by flash chromatography on silicagel (CH2Cl2/MeOH: 97/3). After concentration of the desired fractions, the residue was crystallised in di-isopropyl ether to afford 0.310 g (yield 65%) of the title compound as white crystals.

Workup

  1. temperatureto reflux for 5 h
  2. customThe excess of pyrrolidine was removed in vacuo
  3. customthe residue was purified by flash chromatography on silicagel (CH2Cl2/MeOH: 97/3)
  4. customAfter concentration of the desired fractions, the residue was crystallised in di-isopropyl ether

Sources & evidence

ORD record
ord-4874bd77a6944164aaa1bfc82133d261
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

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