Sodium Hydroxide → HCID 178422438, compound

HRID 1176853Notes

Reaction equation

HRID 1176853 reaction equation
C[O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH3:22])=[C:12]([F:23])[C:8]2[NH:9][CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO.C(OCC)(=O)C.O>[F:23][C:12]1[C:8]2[NH:9][CH:10]=[N:11][C:7]=2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[CH3:22]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 178497004HCID 178497004, compound

Product 1

HCID 178422438HCID 178422438, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

7-Fluoro-6-(4-bromo-2-methyl-phenylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester 8a (63 mg, 0.167 mmol) is suspended in MeOH (1.5 mL) and 20% NaOH (400 μl) is added. After 16 hours, the reaction is cooled to 0° C. and 1 N NCl solution is added dropwise until pH is 2 to 3. The reaction mixture is diluted with ethyl acetate and water and the layers separated. The organic layer is washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give 58 mg (95%) of desired product: MS APCI (+) m/z 366, 364 (M+1 Br pattern) detected; MS APCI (−) m/z 364, 362 (M−1 Br pattern) detected.

Workup

  1. addition1 N NCl solution is added dropwise until pH is 2 to 3
  2. customthe layers separated
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35598628c3bf421e88ebdfa349970586
Source dataset
uspto-grants-2010_11
Patent number
US07842816B2

Reaction notes

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