Pyridine → Diethyl [(6-isobutyramido-4-quinazolinylamino)methylene]propanedioate

HRID 1719941노트

반응식

HRID 1719941 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].N1C=CC=CC=1.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>ClCCl>[C:31]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:35])[CH:32]([CH3:34])[CH3:33]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 20266113Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate

생성물 1

HCID 13060487Diethyl [(6-isobutyramido-4-quinazolinylamino)methylene]propanedioate수율 42.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of diethyl [(6-amino-4-quinazolinylamino)methylene]propanedioate (2.5 g), pyridine (1.2 g) and dichloromethane (55 ml) was stirred under ice-cooling. To the reaction mixture was added dropwise isobutyryl chloride (1.06 g). The reaction mixture was stirred under ice-cooling for 30 minutes and at ambient temperature for 20 minutes. After ice-water was added to the reaction mixture, the resultant mixture was stirred and extracted with chloroform. Insoluble materials were removed by filtration from the extracts. The extracts were washed three times with water and with aqueous solution saturated with sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by a column chromatography using silica gel (developing solvent: chloroform) and crystallized from a mixture of chloroform and hexane to give crystalline diethyl [(6-isobutyramido-4-quinazolinylamino)methylene]propanedioate (1.28 g). Crystals (0.67 g) of the same compound were recovered from the mother liquor by substantially the same crystallization as mentioned above.

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred under ice-
  3. extractionextracted with chloroform
  4. customInsoluble materials were removed by filtration from the extracts
  5. washThe extracts were washed three times with water
  6. dry with materialwith aqueous solution saturated with sodium chloride, dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by a column chromatography
  9. customcrystallized from a mixture of chloroform and hexane

출처 및 근거

ORD 기록
ord-c989cd33c7084b849b77b031751f09eb
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04543356

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