Hydrochloric Acid → 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylic acid

HRID 1861866Notes

Reaction equation

HRID 1861866 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][N:14]3[C:18]4[CH:19]=[CH:20][C:21]([C:23]([O:25]C)=[O:24])=[CH:22][C:17]=4[NH:16][C:15]3=[O:27])=[CH:10]2)=[CH:5][CH:4]=1)#[N:2].[Li+].[OH-].Cl>CC#N.CO>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][N:14]3[C:18]4[CH:19]=[CH:20][C:21]([C:23]([OH:25])=[O:24])=[CH:22][C:17]=4[NH:16][C:15]3=[O:27])=[CH:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18621644methyl 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylate

Product 1

HCID 186216491-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of methyl 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)—benzimidazole-5-carboxylate (82 mg, 0.23 mmol) in CH3CN (2.5 mL) and methanol (2 mL) was added 1N LiOH (2.3 mL, 10 eq.). The reaction mixture was stirred at room temperature for 3 days, acidified with 1N HCl (2.4 mL), filtered and dried to yield 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)—benzimidazole-5-carboxylic acid (72 mg, 91%) as a white solid. 1H NMR(CDCl3) δ: 5.16 (s, 2H); 6.77-6.79 (d, 1H); 7.50-7.54 (t, 2H); 7.62-7.64 (dd, 1H); 7.68 (s, 1H); 7.72 (s, 1H); 7.78-7.84 (dd, 2H); 8.11 (s, 1H); 10.8 (s, 1H). ES-MS (M+H)+=344.1.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-65647f2c7a0944c8858d1adff5716143
Source dataset
uspto-grants-2003_03
Patent number
US06534535B1

Reaction notes

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