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

HRID 323212Notes

Reaction equation

HRID 323212 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]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28]3[N:32]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[C:31]4[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=4[N:29]=3)[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].[CH3:52][S:53]([OH:56])(=[O:55])=[O:54].C(OCC)C>C(OCC)(=O)C>[CH3:52][S:53]([OH:56])(=[O:55])=[O:54].[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]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([NH:27][C:28]3[N:32]([CH2:33][C:34]4[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=4)[C:31]4[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=4[N:29]=3)[CH2:25][CH2:26]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 98748221-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Product 1

HCID 220091421-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (0.45 g) and ethyl acetate (35 mL). Add dropwise a solution of methanesulfonic acid (0.24 g, 2.6 mmol) in ethyl acetate (2.5 mL). After 18 hours, add diethyl ether (100 mL) to form a solid. Repeatedly, decant solvent and add diethyl ether. Again, decant solvent, add diethyl ether, and evaporate in vacuo to give a solid. Dry the solid in vacuo at 82° C. to give the title compound: mp; 131-136° C.

Workup

  1. customto form a solid
  2. customRepeatedly, decant solvent
  3. additionadd diethyl ether
  4. customAgain, decant solvent
  5. additionadd diethyl ether
  6. customevaporate in vacuo
  7. customto give a solid
  8. customDry the solid in vacuo at 82° C.

Sources & evidence

ORD record
ord-20f9ff33f36349a7825a161fa977c597
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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