Sodium Hydroxide → HCID 59267503, compound

HRID 1945293Notes

Reaction equation

HRID 1945293 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:27][CH:26]=2)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=3)[C:18]([O:20]C)=[O:19])[NH:9][C:8]=2[CH:24]=1>CO>[Cl:3][C:4]1[C:5]([C:25]2[CH:26]=[CH:27][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:29][CH:30]=2)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=3)[C:18]([OH:20])=[O:19])[NH:9][C:8]=2[CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68659508HCID 68659508, compound

Product 1

HCID 59267503HCID 59267503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

NaOH (5M in water) (0.12 mL, 0.600 mmol) was added to a solution of methyl 5-{[6-chloro-5-(3′-fluorobiphenyl-4-yl)-1H-benzimidazol-2-yl]oxy}-2-methylbenzoate (8.5 mg, 0.017 mmol) in MeOH (1 mL). The reaction was stirred at 50° C. for 2 h. Volatiles were removed. The residue was partitioned between EtOAc and water. The aqueous phase was acidified to pH=1 with 2 N aqueous HCl and extracted with ethyl acetate (3×30 mL). Combined organics were dried (MgSO4), filtered and concentrated to obtain the desired product. LC-MS: calculated for C27H18ClFN2O3 472.10, observed m/e 473.2 (M+H)+ (Rt: 2.28 min). 1 H NMR (500 MHz, CD3OD): δ7.90 (d, 1H), 7.70 (d, 2H), 7.40-7.55 (m, 9H), 7.05 (t, 1H), 2.61 (s, 3H).

Workup

  1. customVolatiles were removed
  2. customThe residue was partitioned between EtOAc and water
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialCombined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6c2ebb36aa8441db5b8967e3311cabf
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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