Sodium Hydroxide → HCID 178524162, compound

HRID 2064610Notes

Reaction equation

HRID 2064610 reaction equation
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[NH:9][C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][N:13]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>O1CCCC1.O>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([C:10]2[NH:9][C:8]3[CH:21]=[CH:22][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)=[N:13]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497351HCID 178497351, compound

Product 1

HCID 178524162HCID 178524162, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3-(5-methoxycarbonyl-1H-benzoimidazol-2-yl)-1H-indazole [84.5 mg, Example 235(ac)] and sodium hydroxide (74 mg) in tetrahydrofuran (4 mL) and water (2 mL) was heated at 75° C. overnight. The reaction mixture was evaporated and the oily residue was partitioned between ethyl acetate and water. The aqueous layer was acidified to pH 6 and extracted with ethyl acetate. The organic layers was dried over magnesium sulfate and then evaporated to give [2-(indazol-3-yl)-1H-benzoimidazol-5-yl]-carboxylic acid (80 mg) as an oil. MS: 279.14 (M+H)+. HPLC (METHOD H): RT=2.81 minutes.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe oily residue was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layers was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ed264db3776445da8d2d0054df641843
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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