Diethyl Ether → 1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)pyrrolidine methanesulfonic acid salt

HRID 323274Notes

Reaction equation

HRID 323274 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])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([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)[CH2:9]1)=[O:7].[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].C(OCC)C>C(OCC)(=O)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])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([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)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 98312171-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)pyrrolidine

Product 1

HCID 220094681-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)pyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)pyrrolidine (0.45 g, 0.67 mmol) and methanesulfonic acid (0.14 g, 1.4 mmol) in ethyl acetate (5 mL). Heat to reflux. After 1 hour, allow to cool to ambient temperature. After 12 hours, add diethyl ether to give a solid. Collect the solid by filtration to give, after drying, the title compound.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 12 hours
  3. customto give a solid
  4. customCollect the solid
  5. filtrationby filtration
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-ab609cf1ad5340ec81c499d21aa2b913
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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