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

HRID 246645Notes

Reaction equation

HRID 246645 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[N:16]=[C:15]4[C:17]([C:28]([O:30]C)=[O:29])=[CH:18][N:19](COC(=O)C(C)(C)C)[C:14]4=[N:13][CH:12]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[K+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[N:16]=[C:15]4[C:17]([C:28]([OH:30])=[O:29])=[CH:18][NH:19][C:14]4=[N:13][CH:12]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71280196methyl 2-(6-chloro-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 1

HCID 712803892-(6-chloro-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidYield 124.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-(6-chloro-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (202 mg, 0.457 mmol) and KOH (385 mg, 6.86 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was heated to reflux for 3 hours. Reaction mixture was concentrated and the residue was adjusted to pH=5 with 1.0 M HCl aqueous. The precipitate was collected by filtration and dried to afford 2-(6-chloro-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (178 mg, crude) as a yellow solid. LCMS: (M+H)+=314.

Workup

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

Sources & evidence

ORD record
ord-1b60a7d259e042f0badfb6e07273bf9d
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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