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

HRID 512484

반응식

HRID 512484 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b72d0823ea248539d5f0eea4d1780f9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102624B2

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