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

HRID 246661Notes

Reaction equation

HRID 246661 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[C:4]([C:15]2[N:20]=[C:19]3[C:21]([C:32]([O:34]C)=[O:33])=[CH:22][N:23](COC(=O)C(C)(C)C)[C:18]3=[N:17][CH:16]=2)=[N:3]1.[OH-].[K+]>O1CCOCC1.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:13])([F:14])[F:12])[CH:9]=2)[C:4]([C:15]2[N:20]=[C:19]3[C:21]([C:32]([OH:34])=[O:33])=[CH:22][NH:23][C:18]3=[N:17][CH:16]=2)=[N:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71279523methyl 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 1

HCID 712797642-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidYield 155.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyl oxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (200 mg, 0.409 mmol) and KOH (229 mg, 4.09 mmol) in 1,4-dioxane (5 mL) and water (2 mL) was heated to reflux for 4 hours. Dioxane was concentrated and the residual aqueous layer was adjusted to pH=4 with 1.0 M HCl. The precipitate was collected by filtration and dried to afford 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (230 mg, crude) as a yellow solid. LCMS: (M+H)+=362.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. concentrationDioxane was concentrated
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-0b3690a6491c4273bb433131a84df003
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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