Hydrochloric Acid → 1-[5-cyano-2-propyl-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]pyrrole-2-carboxylic acid

HRID 248637Notes

Reaction equation

HRID 248637 reaction equation
[C:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([O:36]C)=[O:35])#[N:2].[OH-].[Na+].Cl>O1CCCC1CO>[C:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:22][N:23]=[N:24][N:25]=3)=[CH:11][CH:10]=2)[C:6]([CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([OH:36])=[O:35])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178440174Methyl 1-[5-cyano-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazol-4-yl]-1H-pyrrole-2-carboxylate

Product 1

HCID 1784401751-[5-cyano-2-propyl-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A solution of methyl 1-[5-cyano-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazol-4-yl]1H-pyrrole-2-carboxylate (Example 35) in tetrahydrofuran-methanol (2:1) was treated with two equivalents of 1N NaOH at 0° C. The reaction mixture was stirred at reflux for 20 hours then treated with two equivalents of 1N HCl. The reaction mixture was then partitioned between ethyl acetate and brine and the organic layer is dried over MgSO4 and evaporated to afford the title compound. MS (FAB, thioglycerol) 479 (M+1).

Workup

  1. temperatureat reflux for 20 hours
  2. customThe reaction mixture was then partitioned between ethyl acetate and brine
  3. dry with materialthe organic layer is dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-dc970fc6aeac40a5929369a1dc67c995
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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