Methanesulfonic Acid → 1-(3,4,5-Trimethoxybenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)-5-oxopyrrolidine methanesulfonic acid salt

HRID 323307Notes

Reaction equation

HRID 323307 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[CH2:6][N:7]1[C:11](=[O:12])[CH2:10][C:9]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([NH:28][C:29]3[N:33]([CH2:34][CH2:35][O:36][CH2:37][CH3:38])[C:32]4[CH:39]=[CH:40][CH:41]=[CH:42][C:31]=4[N:30]=3)[CH2:24][CH2:23]2)([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1.[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].C(OCC)(=O)C>C(OCC)C>[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH3:49][O:48][C:44]1[CH:43]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:45]=1[O:46][CH3:47])[CH2:6][N:7]1[C:11](=[O:12])[CH2:10][C:9]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([NH:28][C:29]3[N:33]([CH2:34][CH2:35][O:36][CH2:37][CH3:38])[C:32]4[CH:39]=[CH:40][CH:41]=[CH:42][C:31]=4[N:30]=3)[CH2:24][CH2:23]2)([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 98528151-(3,4,5-trimethoxybenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)-5-oxopyrrolidine

Product 1

HCID 220093901-(3,4,5-Trimethoxybenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)-5-oxopyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)-5-oxopyrrolidine (0.031 g, 0.05 mmol), methanesulfonic acid (9 mg, 0.097 mmol), and ethyl acetate (2 mL). Heat to reflux. After 1 hour, cool to ambient temperature and add diethyl ether (10 mL) to give a solid. After stirring for 4 hours, decant the solvent. Collect the solid by filtration, rinse with diethyl ether, and dry to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customto give a solid
  3. customdecant the solvent
  4. customCollect the solid
  5. filtrationby filtration
  6. washrinse with diethyl ether
  7. customdry

Sources & evidence

ORD record
ord-2b96c8c7900443339afabedf30b94c2e
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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