Methanol → 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid

HRID 1784005Notes

Reaction equation

HRID 1784005 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[N:13]([N:18]=[CH:19][N:20]=3)[C:14]([Br:17])=[CH:15][N:16]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+].CO>C1COCC1.O>[Br:17][C:14]1[N:13]2[N:18]=[CH:19][N:20]=[C:12]2[C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:21])=[O:2])=[CH:9][CH:8]=2)=[N:16][CH:15]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 575900274-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid methyl ester

Product 1

HCID 575900854-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acidYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid methyl ester (460 mg, 1.32 mmol) is suspended in THF (11 mL) and a solution of lithium hydroxide monohydrate (554 mg, 13.2 mmol) in water (11 mL) is added. The reaction mixture is stirred at room temperature for 4 hours then methanol (11 mL) is added and the mixture is stirred at 50° C. for 24 hours. The mixture is partitioned between water and DCM, the aqueous phase is acidified with 2M HCl (pH 2) and a yellow precipitate is formed. The precipitate is collected by filtration, washed with water and diethyl ether and dried to afford the title compound (215 mg, 49%).

Workup

  1. stirringthe mixture is stirred at 50° C. for 24 hours
  2. customThe mixture is partitioned between water and DCM
  3. customa yellow precipitate is formed
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-2e1ed6dc46e549f8adcab4603cc91303
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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