Hydrochloric Acid → [7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid

HRID 488742Notes

Reaction equation

HRID 488742 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]12[CH2:23][CH2:22][CH2:21][CH2:20][C:7]1([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=1)[NH:8][C:9](=[O:19])[N:10]2[C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1)C.[Li+].[OH-].Cl>CO.O>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:7]23[CH2:20][CH2:21][CH2:22][CH2:23][C:6]2([CH2:5][C:4]([OH:33])=[O:3])[N:10]([C:11]2[CH:12]=[C:13]([Cl:18])[CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:9](=[O:19])[NH:8]3)=[CH:26][CH:27]=1)#[N:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69786744[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid ethyl ester

Product 1

HCID 22268050[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acidYield 12.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid ethyl ester (34 mg) (0.07 mmol) and LiOH (3.0 mg) (1.1 eq) in a 1:1 mixture of MeOH/H2O (4 ml) (5 ml) were stirred 4 days. The reaction mixture was acidified with an aqueous solution of HCl 1N, then concentrated. The residue was purified on HPLC to give [7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid (3.9 mg) as a white solid. 1H NMR (CDCl3): 7.55 (2H, d), 7.25 (2H, d), 7.15 (1H, m), 6.75 (2H, m), 5.0 (1H, m), 4.45 (1H, d), 3.83 (1H, d), 3.05 (1H, d), 2.9 (1H, d), 2.5-2.1 (2H, m), 2.1-1.8 (4H, m).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on HPLC

Sources & evidence

ORD record
ord-32e0a529d17e46e48f3315c2fffcc308
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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