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

HRID 323191Notes

Reaction equation

HRID 323191 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([NH:31][C:32]3[N:36]([CH2:37][CH2:38][O:39][CH2:40][CH3:41])[C:35]4[CH:42]=[CH:43][CH:44]=[CH:45][C:34]=4[N:33]=3)[CH2:27][CH2:26]2)([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:9]1)=[O:7].C(OCC)(=O)C.[CH3:59][S:60]([OH:63])(=[O:62])=[O:61]>C(OCC)C>[CH3:59][S:60]([OH:63])(=[O:62])=[O:61].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH:28]([NH:31][C:32]3[N:36]([CH2:37][CH2:38][O:39][CH2:40][CH3:41])[C:35]4[CH:42]=[CH:43][CH:44]=[CH:45][C:34]=4[N:33]=3)[CH2:29][CH2:30]2)([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 98965901-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dimethoxyphenyl)pyrrolidine

Product 1

HCID 220094851-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dimethoxyphenyl)pyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dimethoxyphenyl)pyrrolidine (0.48 g, 0.67 mmol) and ethyl acetate. Add a solution of methanesulfonic acid (2.2 mL, 0.77 M in ethyl acetate, 1.7 mmol). After 24 hours, add diethyl ether (150 mL) to form a solid. Decant solvent, add diethyl ether (200 mL) and stir. After 5 hours, decant solvent, add diethyl ether (200 mL). After 24 hours, collect the solid by filtration and dry in vacuo to give the title compound: mp; 125-130° C. Elemental Analysis calculated for C40H53N5O7 . 2 CH3SO3H . 2.43 H2O: C 53.00; H 6.97; N 7.36; Found: C 53.38; H 6.65; N 7.39.

Workup

  1. customto form a solid
  2. waitAfter 5 hours
  3. customdecant solvent
  4. additionadd diethyl ether (200 mL)
  5. waitAfter 24 hours
  6. customcollect the solid
  7. filtrationby filtration
  8. customdry in vacuo

Sources & evidence

ORD record
ord-1f57dcb5350045a2bd049ebd54a608ee
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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