Diethyl Ether → 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 323500Notes

Reaction equation

HRID 323500 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)C>C(OCC)(=O)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 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 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 8857Ethyl AcetateSolvent

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) and methanesulfonic acid (0.17 g, 1.8 mmol) in ethyl acetate (10 mL). Heat to reflux. After 1 hour, cool to ambient temperature, add diethyl ether (75 mL). After 12 hours, evaporate the solvent to give a residue. Triturate the residue with diethyl ether (80 mL) to give a solid. Collect the solid and dry to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 12 hours
  3. customevaporate the solvent
  4. customto give a residue
  5. customTriturate the residue with diethyl ether (80 mL)
  6. customto give a solid
  7. customCollect the solid
  8. customdry

Sources & evidence

ORD record
ord-84938087964e4fd7b8ba0437d9c481a7
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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