Sodium Hydroxide → HCID 68089368, compound

HRID 1772026Notes

Reaction equation

HRID 1772026 reaction equation
[NH:1]=[C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][N:3]1[NH2:12].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[OH-].[Na+].[OH:28][CH2:29][C:30](OC)=O>CCO>[N:1]1[C:30]([CH2:29][OH:28])=[N:12][N:3]2[C:2]=1[C:11]1[N:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:5]=[CH:4]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66774Methyl GlycolateHCID 866678148-imino-1,7-naphthyridin-7(8H)-amine 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 68089368HCID 68089368, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 8-imino-1,7-naphthyridin-7(8H)-amine-2,4,6-trimethylbenzenesulfonate (1.2 g, 2.83 mmol) in EtOH (30 mL) was added NaOH (227 mg, 5.67 mmol). The mixture was stirred at 60° C. for 1 h. Then methyl 2-hydroxyacetate (773 mg, 8.50 mmol) was added. The resulting mixture was stirred at reflux for 2 h. The mixture was concentrated and purified by silica gel column chromatography (eluting with DCM/MeOH v/v 30:1) to give [1,2,4]triazolo[1,5-h][1,7]naphthyridin-2-ylmethanol as a yellow solid (280 mg, yield 49%). ESI MS: m/z 201.1 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel column chromatography (
  5. washeluting with DCM/MeOH v/v 30:1)

Sources & evidence

ORD record
ord-88bb48df55c4477fac864b25f0d555c2
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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