4-Aminopyridine → HCID 54036429, compound

HRID 363040Notes

Reaction equation

HRID 363040 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=2[CH2:18][CH2:19][CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>CN(C=O)C.CCOC(C)=O>[N:31]1[CH:32]=[CH:33][C:28]([NH:27][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][C:9]([O:8][CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:10]([CH2:18][CH2:19][CH3:20])[CH:11]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 53750496HCID 53750496, compound

Product 1

HCID 54036429HCID 54036429, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 22-6 (770 mg, 2.78 mmol) in 10 mL of (CH2Cl)2 and 0.05 mL of DMF was added 0.26 mL (3.05 mmol) of oxalyl chloride. The resulting solution was heated at 50° C. for 30 min, cooled to 0° C. and treated with 1.20 g (13.8 mmol) of 4-aminopyridine. Stirring was continued for 2 h before the heterogeneous mixture was diluted with 50 mL of EtOAc and quenched with 25 mL of 5% Na2CO3. The organic extract was washed with sat'd NH4Cl (3×50 mL), water (2×25 mL), brine (25 mL) and dried over MgSO4. Evaporation of the solvent and column chromatography (EtOAc) afforded product 22-7.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with 25 mL of 5% Na2CO3
  3. extractionThe organic extract
  4. washwas washed with sat'd NH4Cl (3×50 mL), water (2×25 mL), brine (25 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent and column chromatography (EtOAc)

Sources & evidence

ORD record
ord-04c6e0f1aa4b451aa6a8e5fbcd12460d
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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