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

HRID 323282Notes

Reaction equation

HRID 323282 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[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[N:34]([CH2:35][CH2:36][O:37][CH2:38][CH3:39])[C:33]4[CH:40]=[CH:41][CH:42]=[CH:43][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:44].C(OCC)(=O)C.[CH3:58][S:59]([OH:62])(=[O:61])=[O:60]>C(OCC)C>[CH3:58][S:59]([OH:62])(=[O:61])=[O:60].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[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[N:34]([CH2:35][CH2:36][O:37][CH2:38][CH3:39])[C:33]4[CH:40]=[CH:41][CH:42]=[CH:43][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:44]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 99181341-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

Product 1

HCID 220093031-(3,4,5-Trimethoxybenzyl)-3-(3-(4-(1-(2-ethoxyethyl)-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-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine (0.91 g, 1.28 mmol) and ethyl acetate (15 mL). Add methanesulfonic acid (0.25 g, 2.57 mmol) and heat to reflux. After 1 hour, cool to ambient temperature and stir. After 12 hours, add diethyl ether and decant the solvent. Repeatedly, add diethyl ether and decant to give a solid. Collect the solid by filtration and dry in vacuo to give the title compound. Rf=0.24 (silica gel, 10% methanol/ethyl acetate/2% triethylamine).

Workup

  1. waitAfter 12 hours
  2. customdecant the solvent
  3. additionRepeatedly, add diethyl ether
  4. customdecant
  5. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. customdry in vacuo

Sources & evidence

ORD record
ord-9f7aacea7c134c27ad7c2ae971a3b45b
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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