Pyridine → HCID 10644118, compound

HRID 1779957Notes

Reaction equation

HRID 1779957 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.N1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16](=[O:19])([O-])[OH:17].[Na+].[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C)C1C=CN=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:25]([C:24]2[CH:3]=[C:2]3[C:11]([CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:17][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:19])[CH2:9]3)=[CH:22][CH:23]=2)=[O:21])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 133964-AminobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 10644118HCID 10644118, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In 5 ml of toluene, 0.7 g of the compound obtained in the step (5-6) and 1.5 ml of oxalyl chloride were dissolved and a drop of N,N-dimethylformamide was added. The mixture was stirred for an hour at room temperature. The solvent was distilled off under reduced pressure to obtain corresponding acid chloride. Acid chloride thus obtained was dissolved in 5 ml of tetrahydrofuran, and 0.35 g of 4-aminobenzonitrile, 1 ml of pyridine and 50 mg of 4-dimethylaminopyridine were added. The mixture was stirred for 4 hours at room temperature. The reaction mixture was mixed with on aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extracted chloroform solution was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crude product. The crude product was purified by silica gel column chromatography using a mixture, chloroform:ethyl acetate=5:1, as a developer to yield 0.47 g of the entitled compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extracted chloroform solution was dried with anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customto obtain crude product
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d00cef5f3af346f1ab6b35ed2540f235
Source dataset
uspto-grants-1997_05
Patent number
US05629321

Reaction notes

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