3-Pyridinecarboxaldehyde → HCID 136613153, compound

HRID 570912Notes

Reaction equation

HRID 570912 reaction equation
[NH2:1][N:2]1[CH2:7][C:6](/[CH:8]=[N:9]/[O:10][CH3:11])=[N:5][NH:4][C:3]1=[O:12].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1>CCO.Cl>[CH3:11][O:10]/[N:9]=[CH:8]/[C:6]1[CH2:7][N:2](/[N:1]=[CH:19]/[C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[C:3](=[O:12])[NH:4][N:5]=1

Participants

5

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 136613157HCID 136613157, compound

Product 1

HCID 136613153HCID 136613153, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-amino-6-[(E)-methoxyiminomethyl]-2,5-dihydro-1,2,4-triazin-3-one (2.57 g, 15.0 mmol) in EtOH was added pyridine-3-carbaldehyde (1.41 mL, 15.0 mmol), followed by addition of 1 drop conc. HCl. The mixture was heated to 60° C. for 3 h and then allowed to cool to room temperature. After addition of silica gel, the reaction mixture was evaporated and purified by flash chromatography (5% MeOH/CH2Cl2) to give compound I-001 as a white solid. LCMS (Method H) RT 0.97 min. [M+H]+ 261. M.p. 237-238° C.

Workup

  1. temperatureto cool to room temperature
  2. additionAfter addition of silica gel
  3. customthe reaction mixture was evaporated
  4. custompurified by flash chromatography (5% MeOH/CH2Cl2)
  5. customto give compound I-001 as a white solid
  6. customLCMS (Method H) RT 0.97 min. [M+H]+ 261

Sources & evidence

ORD record
ord-b5eee383e07d4ad694232206fef88133
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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