Potassium Hydroxide → 2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

HRID 246670Notes

Reaction equation

HRID 246670 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:29]([O:31]C)=[O:30])=[CH:19][N:20](COC(=O)C(C)(C)C)[C:15]3=[N:14][CH:13]=2)=[N:3]1.[OH-].[K+]>O1CCOCC1.O.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:29]([OH:31])=[O:30])=[CH:19][NH:20][C:15]3=[N:14][CH:13]=2)=[N:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71279823methyl 2-(1,6-dimethyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 1

HCID 712798782-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidYield 84.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of methyl 2-(1,6-dimethyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (1 g, 2.3 mmol) in dioxane/H2O (40 mL/10 mL) was added a solution of KOH (1.39 g, 34.5 mmol) in water (10 mL) at room temperature. Then the reaction mixture was heated to reflux for 4 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was diluted with water and acidified to pH 3-4 with HCl (aqueous, 2 M). The mixture was filtered and the filter cake dried to give 2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (0.6 g, 84.5%) as a solid, which was used in the next step without further purification. MS: (M+H)+=308.1.

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. filtrationThe mixture was filtered
  6. customthe filter cake dried

Sources & evidence

ORD record
ord-044386a29bc048a39a44a4fdf1bbcbb9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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