2-Thiophenecarboxaldehyde → HCID 69926893, compound

HRID 2120129Notes

Reaction equation

HRID 2120129 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[N:6][CH:5]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:25])(=O)=O.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=O.[OH-].[K+]>O1CCOCC1.CO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([NH2:10])[C:7]2[N:6]([N:25]=[C:32]([C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)[N:11]=2)[CH:5]=1)=[O:12]

Participants

7

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 14797Potassium HydroxideHCID 9920476Methyl 5,6-diaminopyridine-3-carboxylateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 69926893HCID 69926893, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.114 g (6.66 mmol) 5,6-diamino-nicotinic acid methyl ester in 40 ml dioxane was treated with 1.578 g (7.33 mmol) O-mesitylenesulfonylhydroxylamine (prepared from ethyl-o-mesitylenesulfonylacetohydroxamate and HClO4 (70%)) for 1 h at room temperature. 0.897 g (8 mmol) thiophene-2-carboxaldehyde and molecular sieves 4 Å was added and heated to 100° C. for 4 h before addition of 1.6 ml 5M KOH in methanol. The mixture was heated to 70° C. for 2 h and stirred at room temperature for 14 h. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography on silica eluting with a mixture of ethyl acetate and n-hexane to yield after evaporation 0.88 g (48%) of the title compound.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica eluting with a mixture of ethyl acetate and n-hexane
  3. customto yield
  4. customafter evaporation 0.88 g (48%) of the title compound

Sources & evidence

ORD record
ord-5ecbac5c48a9418f89800e2ecb473926
Source dataset
uspto-grants-2004_02
Patent number
US06689790B2

Reaction notes

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