Sodium Hydroxide → HCID 178524162, compound

HRID 2182366Notes

Reaction equation

HRID 2182366 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. (b) 3-(5,6-Dimethyl-1H-benzoimidazol-5-yl)-pyrazole-4-carboxylic acid

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-58de98224487417889b7547f82bea6be
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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