Hydrochloric Acid → Methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylic acid

HRID 592324Notes

Reaction equation

HRID 592324 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[N:15]=[C:14]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[N:13]([CH3:22])[C:12]=3[CH:11]=[C:10]([C:23]([O:25]C)=[O:24])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[CH3:30]O>>[CH3:30][C:9]1[C:10]([C:23]([OH:25])=[O:24])=[CH:11][C:12]2[N:13]([CH3:22])[C:14]([CH2:17][C:18]([OH:21])([CH3:19])[CH3:20])=[N:15][C:16]=2[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66689966Methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylate

Product 1

HCID 66689965Methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylic acid

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylate (83.7 mg, 0.235 mmol) in MeOH (0.500 mL) was added sodium hydroxide (0.705 mL, 1M, 0.705 mmol). Reaction heated in the microwave at 100° C. for 15 min. HCl (0.352 mL, 2M, 0.705 mmol) was added and the reaction mixture was concentrated. Title compound used as-is with three sodium chloride salts without further purification (122 mg): LC-MS [M+1]=343.2.

Workup

  1. customReaction
  2. concentrationthe reaction mixture was concentrated
  3. customwithout further purification (122 mg)

Sources & evidence

ORD record
ord-6250d41e5e6b4c77b1f921147e36779b
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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