Picolinic acid → HCID 14390488, compound

HRID 621838Notes

Reaction equation

HRID 621838 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[C:24]([NH:29][CH2:30][C:31]([NH2:33])=[O:32])=[N:25][CH:26]=[CH:27][CH:28]=1.[N-]1C=CN=C1>O1CCCC1.C(#N)C>[NH2:33][C:31](=[O:32])[CH2:30][NH:29][C:24]1[C:23]([NH:22][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 14390487HCID 14390487, compound

Product 1

HCID 14390488HCID 14390488, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

While bubbling nitrogen through a solution of picolinic acid (1.23 g, 0.01 mole) in 100 ml of tetrahydrofuran, solid 1,1'-carbonyldiimidazole (1.62 g, 0.01 mole) was added in portions. The reaction mixture was allowed to stir at room temperature for 5 hours. Then, a solution of 2-[(3-amino-2-pyridinyl)amino]acetamide (1.66 g, 0.01 mole) in acetonitrile was added in portions to the imidazolide solution and the reaction mixture was allowed to stir at room temperature overnight. The solvents were evaporated. The residue completely solidified upon standing. The solid was washed with methylene chloride and the solid was filtered off. The solid was recrystallized from ethyl acetate to give several crops of crystals, which were combined and recrystallized from ethyl acetate to give 0.52 g of title compound, mp 188°-90° C. with decomposition.

Workup

  1. additionwas added in portions
  2. stirringto stir at room temperature overnight
  3. customThe solvents were evaporated
  4. washThe solid was washed with methylene chloride
  5. filtrationthe solid was filtered off
  6. customThe solid was recrystallized from ethyl acetate
  7. customto give several crops of crystals, which
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-afbfe14b404b48ee8c0b98ab93759228
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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