Hydrochloric Acid → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt

HRID 323481Notes

Reaction equation

HRID 323481 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:43]([N:46]2[CH:50]=[N:49][N:48]=[N:47]2)=[CH:42][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:27]3[N:31]([CH2:32][C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)[C:30]4[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=4[N:28]=3)[CH2:22][CH2:21]2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)=[O:6].CO.[ClH:53].O1CCOCC1>C(OCC)C.ClCCl>[ClH:53].[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:43]([N:46]2[CH:50]=[N:49][N:48]=[N:47]2)=[CH:42][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:27]3[N:31]([CH2:32][C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)[C:30]4[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=4[N:28]=3)[CH2:22][CH2:21]2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 98312321-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Product 1

HCID 702432601-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Combine 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (0.22 g, 0.33 mmol) and methanol (4 mL). Add a solution of hydrochloric acid in dioxane (0.166 mL, 4 M, 0.62 mmol). After 18 hours, evaporate in vacuo to give a residue. Three times, combine the residue and dichloromethane and evaporate in vacuo to give a residue. Combine the residue and dichloromethane (about 2 mL) slowly add, with stirring, to diethyl ether (40 mL) to give a solid. Collect the solid by filtration and dry in vacuo to give the title compound: mp; 184-206° C.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. customevaporate in vacuo
  4. customto give a residue
  5. additionslowly add
  6. customto give a solid
  7. customCollect the solid
  8. filtrationby filtration
  9. customdry in vacuo

Sources & evidence

ORD record
ord-a347d67886c04da48699dea9afd48a84
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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