Hydrochloric Acid → 1-(4-Cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 512484

Reaction equation

HRID 512484 reaction equation
C[N:2]([CH:4]=[C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[O:7][C:6]1=[O:13])[CH3:3].Cl.[C:15]([C:17]1[CH:24]=[CH:23][C:20](CN)=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[Na+].Cl>C(O)C>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:3][N:2]2[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:6]([OH:7])=[O:13])=[CH:4]2)=[CH:19][CH:18]=1)#[N:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14897943-(Dimethylaminomethylidene)-6-methylpyran-2,4-dioneHCID 99422504-(Aminomethyl)benzonitrile hydrochlorideHCID 23676156Sodium t-butoxide

Product 1

HCID 867115261-(4-Cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylaminomethylene-6-methyl-pyran-2,4-dione (preparation 1a, 2.00 g, 9.38 mmol based on 85% purity), 4-cyanobenzylamine hydrochloride (4.00 mL, 23.7 mmol) and sodium tert-butoxide (2.74 g, 28.5 mmol) in ethanol (11 mL) is heated for 48 h at 90° C. The reaction mixture is acidified with 4N aqueous HCl and extracted several times with dichloromethane. The combined organic layer is dried over Na2SO4, evaporated under reduced pressure and purified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.). Yield: 0.94 g (37% of theory); ESI mass spectrum: [M+H]+=269; Retention time HPLC: 0.86 min (Z002—005).

Workup

  1. extractionextracted several times with dichloromethane
  2. dry with materialThe combined organic layer is dried over Na2SO4
  3. customevaporated under reduced pressure
  4. custompurified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.)
  5. custom0.86 min (Z002—005)

Sources & evidence

ORD record
ord-1b72d0823ea248539d5f0eea4d1780f9
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Linked notes

Loading…