Sodium Cyanide → 6-(4-Chloro-3-methoxy-phenyl)-2,2-dimethyl-3,6-dioxo-5-pyridin-4-yl-hexanenitrile

HRID 2223097노트

반응식

HRID 2223097 반응식
[CH3:1][C:2]([CH3:15])([C:5](=[O:14])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:3]#[N:4].[C-]#N.[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[O:28][CH3:29].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([C:24](=[O:25])[CH:7]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH2:6][C:5](=[O:14])[C:2]([CH3:15])([CH3:1])[C:3]#[N:4])=[CH:22][C:21]=1[O:28][CH3:29]

참가 물질

7

반응물 4

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 129097254-Chloro-3-methoxybenzaldehydeHCID 691376492,2-Dimethyl-3-oxo-5-pyridin-4-yl-pent-4-enenitrile

생성물 1

HCID 691376796-(4-Chloro-3-methoxy-phenyl)-2,2-dimethyl-3,6-dioxo-5-pyridin-4-yl-hexanenitrile수율 222.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

A solution of the product of Example 1 Step 1 (4.0 g, 20.0 mmol) in DMF (7 ml) was added to a solution of sodium cyanide (300 mg, 6.12 mmol) in DMF (7 ml) over 15 minutes at room temperature. After stirring for a further 15 minutes, a solution of 4-chloro-3-methoxy-benzaldehyde (F. Claudi et al., J. Med. Chem., 1992, 35, 4408) (640 mg, 3.75 mmol) in DMF (6 ml) was added dropwise. The mixture was stirred at room temperature for 18 hours and then diluted with water and the pH of the solution adjusted to 9 with aqueous sodium hydrogen carbonate solution. The mixture was extracted with chloroform and the organic phase washed with water and brine, dried and concentrated in vacuo. The residue was chromatographed on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1) to give the title compound (3.1 g, 42%); MS (ES+) m/e 371, 373 [M+H]+.

후처리

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionThe mixture was extracted with chloroform
  3. washthe organic phase washed with water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1)

출처 및 근거

ORD 기록
ord-b8606eb0ae104e2294f4aee316cf6d52
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375105B2

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