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

HRID 323320Notes

Reaction equation

HRID 323320 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]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][C:36]4[S:37][C:38]([Cl:41])=[CH:39][CH:40]=4)[C:33]4[CH:42]=[CH:43][CH:44]=[CH:45][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].[CH3:53][S:54]([OH:57])(=[O:56])=[O:55].C(OCC)(=O)C>CO>[CH3:53][S:54]([OH:57])(=[O:56])=[O:55].[CH3:52][O:51][C:47]1[CH:46]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:48]=1[O:49][CH3:50])[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][C:36]4[S:37][C:38]([Cl:41])=[CH:39][CH:40]=4)[C:33]4[CH:42]=[CH:43][CH:44]=[CH:45][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 98535341-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(5-chlorothien-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) Pyrrolidine

Product 1

HCID 220092511-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(5-chlorothien-2-ylmethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) pyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(5-chlorothien-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl) pyrrolidine (1.21 g, 1.61 mmol), and methanesulfonic acid (0.23 mL, 3.54 mmol), ethyl acetate (90 mL), and methanol (10 mL) and stir. After 18 hours, filter and evaporate the filtrate in vacuo to give a residue. Triturate the residue with diethyl ether to give a solid. Decant the solvent and add diethyl ether. Collect the solid by filtration and dry in vacuo at 82° C. to give the title compound. Elemental Analysis calculated for C39H42ClF2N5O4S.2 CH3SO3H.1.8 H2O: C, 50.52; H, 5.54; N, 7.18. Found: C, 50.67; H, 5.38; N, 7.22.

Workup

  1. filtrationfilter
  2. customevaporate the filtrate in vacuo
  3. customto give a residue
  4. customTriturate the residue with diethyl ether
  5. customto give a solid
  6. customDecant the solvent
  7. additionadd diethyl ether
  8. customCollect the solid
  9. filtrationby filtration
  10. customdry in vacuo at 82° C.

Sources & evidence

ORD record
ord-613d6facb14b4056845072a6ef365cde
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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