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

HRID 323309Notes

Reaction equation

HRID 323309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[NH:34][C:33]4[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:8]1=[O:39].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].C(OCC)(=O)C>C(OCC)C>[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].[CH3:46][O:45][C:41]1[CH:40]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:42]=1[O:43][CH3:44])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[NH:31][C:32]4[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=4[N:34]=3)[CH2:25][CH2:24]2)([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:8]1=[O:39]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 98954571-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

Product 1

HCID 220091751-(3,4,5-Trimethoxybenzyl)-3-(3-(4-(1h-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine (0.37 g, 0.56 mmol), methanesulfonic acid (0.17 g, 1.8 mmol), and ethyl acetate (10 mL). Heat to reflux. After 1 hour, cool to ambient temperature and add diethyl ether (75 mL). After 12 hour, collect the solid that forms and add diethyl ether (80 mL) and stir. After 12 hours, decant the solvent and collect the solid, rinse with diethyl ether and dry in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 12 hour
  3. customcollect the solid that forms
  4. additionadd diethyl ether (80 mL)
  5. waitAfter 12 hours
  6. customdecant the solvent
  7. customcollect the solid
  8. washrinse with diethyl ether
  9. customdry in vacuo

Sources & evidence

ORD record
ord-556f1a876048470f96dfbda3325ed5c5
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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