3,4-Diaminopyridine → HCID 178478056, compound

HRID 530448Notes

Reaction equation

HRID 530448 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](O)=O)[CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[NH2:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:8]2[NH:18][C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=2)[N:7]=1

Participants

6

Reactant 4

HCID 59183,4-DiaminopyridineHCID 208126-Chloropicolinic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 178478056HCID 178478056, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6-Chloropyridine-2-carboxylic acid (2.00 g, 12.7 mmol), 3,4-diaminopyridine (1.52 g, 14.0 mmol) and DIPEA (2.43 mL, 14.0 mmol) were dissolved in DMF (20 mL) and HBTU (5.29 g, 14.0 mmol) was added. The reaction mixture was stirred for 48 h and concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with 1 M aq Na2CO3 (2×100 mL), water (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography, dissolved in AcOH and heated at 120° C. for 50 min. The solvent was removed in vacuo and the residue was suspended in 1 M aq Na2CO3 (50 mL) and extracted with EtOAc (5×50 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography and recrystallisation from MeOH to give the title compound (534 mg, 37%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 1 M aq Na2CO3 (2×100 mL), water (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. dissolutiondissolved in AcOH
  8. customThe solvent was removed in vacuo
  9. extractionextracted with EtOAc (5×50 mL)
  10. dry with materialThe combined organic fractions were dried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography and recrystallisation from MeOH

Sources & evidence

ORD record
ord-fc97a8d9b7b241b4a5825e5a4853868c
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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