Methanesulfonic Acid → 1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-methylsulfonylethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) pyrrolidine methanesulfonic acid salt

HRID 323327Notes

Reaction equation

HRID 323327 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])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:33]4[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7].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].[CH3:51][O:50][C:46]1[CH:45]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:47]=1[O:48][CH3:49])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][CH2:36][S:37]([CH3:40])(=[O:38])=[O:39])[C:33]4[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 9853348HCID 9853348, compound

Product 1

HCID 220091761-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-methylsulfonylethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) pyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-methylsulfonylethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) pyrrolidine (1.0 g, 1.38 mmol) and ethyl acetate (50 mL). Add methanesulfonic acid (0.27 g, 2.76 mmol). Heat to reflux. After 1 hour, cool to ambient temperature and stir. After 40 hours, add diethyl ether (150 mL) to give a solid. Repeatedly, decant the solvent add diethyl ether before collecting the solid and drying in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 40 hours
  3. customto give a solid
  4. customRepeatedly, decant the solvent
  5. additionadd diethyl ether
  6. custombefore collecting the solid
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-a474e043dcc4479ab42d4422e919f057
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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