6-Acetamidopicolinic acid → HCID 57775728, compound

HRID 1880264Notes

Reaction equation

HRID 1880264 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:14]/[C:15](=[N:36]\O)/[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[CH:27]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1>O1CCOCC1.CN(C=O)C>[C:33]([NH:32][C:28]1[CH:27]=[C:26]([NH:25][S:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]3[N:36]=[C:11]([C:9]4[N:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][CH:8]=4)[O:13][N:14]=3)=[CH:21][CH:20]=2)(=[O:24])=[O:23])[CH:31]=[CH:30][CH:29]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 2

HCID 8246406-Acetamidopicolinic acidHCID 57775722HCID 57775722, compound

Product 1

HCID 57775728HCID 57775728, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Carbonyldiimidazole (9.78 g) dissolved in dioxane (100 ml) is added dropwise to 6-acetylaminopyridine-2-carboxylic acid (10.86 g) in a mixture of dioxane (100 ml) and DMF (60 ml) and the mixture is stirred at room temperature for 3 h. N-{3-[({4-[(Z)-Amino(hydroxyimino)methyl]phenyl}sulfonyl)amino]phenyl}acetamide is then added as a solid and the reaction mixture is stirred at room temperature for 16 h. Subsequently, the reaction mixture is stirred at 100° C. for 4 h and then poured onto ice/water. The product is left to stand for 10 min, collected by filtration, washed with water (three times) and dried in a vacuum oven. 25.55 g (90% of theory) of product are obtained as a solid.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 16 h
  2. stirringSubsequently, the reaction mixture is stirred at 100° C. for 4 h
  3. additionpoured onto ice/water
  4. waitThe product is left
  5. waitto stand for 10 min
  6. filtrationcollected by filtration
  7. washwashed with water (three times)
  8. customdried in a vacuum oven
  9. custom25.55 g (90% of theory) of product are obtained as a solid

Sources & evidence

ORD record
ord-e4637f7046b9474eb0276d1f5c15b166
Source dataset
uspto-grants-2012_11
Patent number
US08318761B2

Reaction notes

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