Diethyl Ether → 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-cyanoethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine Methanesulfonic Acid Salt

HRID 323329Notes

Reaction equation

HRID 323329 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]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][CH2:36][C:37]#[N:38])[C:33]4[CH:39]=[CH:40][CH:41]=[CH:42][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].[CH3:50][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].[CH3:1][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]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([NH:29][C:30]3[N:34]([CH2:35][CH2:36][C:37]#[N:38])[C:33]4[CH:39]=[CH:40][CH:41]=[CH:42][C:32]=4[N:31]=3)[CH2:27][CH2:28]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 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 98099991-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-cyanoethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine

Product 1

HCID 220093871-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-cyanoethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine Methanesulfonic Acid Salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-cyanoethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine (0.11 g, 0.16 mmol) and methanesulfonic acid (0.033 g, 0.34 mmol) in ethyl acetate (5 ml and stir. After 12 hours, add diethyl ether (100 mL) to give a solid. Decant and add diethyl ether. Collect the solid and dry in vacuo to give the title compound.

Workup

  1. customto give a solid
  2. customDecant
  3. additionadd diethyl ether
  4. customCollect the solid
  5. customdry in vacuo

Sources & evidence

ORD record
ord-7ff0aa0fe06d4759adfb5b15e818cedd
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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