4-Aminopyridine → HCID 86700706, compound

HRID 530451Notes

Reaction equation

HRID 530451 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([OH:10])=O)[N:3]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:8]([NH:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 86700706HCID 86700706, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromopyridine-6-carboxylic acid (5.00 g, 24.8 mmol) was dissolved in DCM (100 mL) and DMF (1 mL), and oxalyl chloride (7.54 g, 59.4 mmol) was added dropwise over 5 min. The reaction mixture was stirred for 2 h and the solvents were removed in vacuo. The reaction mixture was azeotroped twice with DCM and dissolved in DCM (100 mL). DIPEA (12.8 g, 99.0 mmol) and 4-aminopyridine (4.66 g, 49.5 mmol) were added dropwise and the reaction mixture was stirred for 2 h, washed with sat aq NaHCO3 (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH to give the title compound (5.00 g, 73%) as an off white solid. LCMS (ES+): 278.2 [MH]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe reaction mixture was azeotroped twice with DCM
  3. dissolutiondissolved in DCM (100 mL)
  4. stirringthe reaction mixture was stirred for 2 h
  5. washwashed
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallised from MeOH

Sources & evidence

ORD record
ord-6453db60e8b1445a86708ef2093d8797
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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