Sodium Hydroxide → 5-[3-Amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazole-2-carboxylic acid

HRID 78662Notes

Reaction equation

HRID 78662 reaction equation
[NH2:1][C:2]1[C:3]([C:20]2[O:24][C:23]([C:25]([O:27]CC)=[O:26])=[N:22][N:21]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[OH-].[Na+]>O>[NH2:1][C:2]1[C:3]([C:20]2[O:24][C:23]([C:25]([OH:27])=[O:26])=[N:22][N:21]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59472382Ethyl 5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 594717155-[3-Amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazole-2-carboxylic acidYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazole-2-carboxylate (50 mg, 0.1198 mmol) in NaOH (59.90 μL of 1 M, 0.05990 mmol) was stirred at room temperature for 1 h. Water (0.5 mL) was added and the reaction mixture stirred at room temperature for 5 min and then filtered. The yellow solid obtained was dried under vacuum to give the product (30.93 mg, 62%); 1H NMR (400 MHz, DMSO) d 1.19 (d, 6H), 3.40-3.49 (m, 1H), 7.90 (br s, 2H), 7.96 (d, 2H), 8.32 (d, 2H) and 9.00 (s, 1H) ppm; MS (ES+) 390.13

Workup

  1. filtrationfiltered
  2. customThe yellow solid obtained
  3. customwas dried under vacuum

Sources & evidence

ORD record
ord-d36f50196de64941bbf65b855b91038a
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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