Sodium Hydroxide → HCID 178426802, compound

HRID 1945286Notes

Reaction equation

HRID 1945286 reaction equation
[Cl:1][C:2]1[C:3]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:4][C:5]2[N:9]=[C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([O:18]C)=[O:17])[NH:7][C:6]=2[CH:22]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:3]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:4][C:5]2[N:9]=[C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([OH:18])=[O:17])[NH:7][C:6]=2[CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178498529HCID 178498529, compound

Product 1

HCID 178426802HCID 178426802, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 5-({6-chloro-5-[(2-fluorophenyl)-ethynyl]-1H-benzimidazol-2-yl}oxy)-2-methylbenzoate (910 mg, 2.1 mmol) and 4.2 mL 5 M aqueous NaOH in 15 mL MeOH and 15 mL water was heated at 70° C. for 30 min. Volatiles were removed. The residue was dissolved in water (30 mL), and acidified with 2 N aqueous HCl, the precipitated solid was filtered (rinsing with water) and dried to afford the desired product as a white solid. LC/MS: calculated for C23H14ClFN2O3 420, observed mile 421 (M+H)+ (2.1/4 min). 1H NMR (500 MHz, CD3OD): δ 7.88-7.16 (9H, m), 2.61 (3H, s).

Workup

  1. customVolatiles were removed
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. filtrationthe precipitated solid was filtered
  4. wash(rinsing with water)
  5. customdried

Sources & evidence

ORD record
ord-7ca5ab2e847e4bbf9bd5f6570a9a5265
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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