Potassium Hydroxide → HCID 71280375, compound

HRID 246629Notes

Reaction equation

HRID 246629 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:16]=[C:15]3[C:17]([C:28]([O:30]C)=[O:29])=[CH:18][N:19](COC(=O)C(C)(C)C)[C:14]3=[N:13][CH:12]=2)=[N:3]1.[OH-].[K+]>O.O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:16]=[C:15]3[C:17]([C:28]([OH:30])=[O:29])=[CH:18][NH:19][C:14]3=[N:13][CH:12]=2)=[N:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71281046HCID 71281046, compound

Product 1

HCID 71280375HCID 71280375, compoundYield 113.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-(1-methyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (150 mg, 0.36 mmol), potassium hydroxide (280 mg, 5 mmol) in 2.5 mL of water and 5 mL of 1,4-dioxane was heated to reflux for 90 mins. The reaction mixture was cooled to room temperature, evaporated, acidified with 1N HCl, then filtered and dried to give 2-(1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (120 mg, crude) as a brown solid. LCMS: (M+H)+=294. Used into the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 mins
  3. customevaporated
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-26094cec4b304dc3aac76cbe809b3814
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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