Ethanol → 6-Amino-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline

HRID 1451882노트

반응식

HRID 1451882 반응식
C(O)C.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2[N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([N+:35]([O-])=O)[CH:31]=3)[N:26]([CH3:38])[C:25]2=[O:39])[CH2:20][CH2:19]1>[Fe].O>[NH2:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:38])[C:25](=[O:39])[N:24]([CH:21]1[CH2:20][CH2:19][N:18]([C:9]3[C:8]4[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([O:5][CH3:4])[CH:7]=4)[N:12]=[CH:11][N:10]=3)[CH2:23][CH2:22]1)[C:33]2=[O:34]

참가 물질

5

반응물 2

HCID 702EthanolHCID 229235503-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-methyl-6-nitro-2,4(1H,3H)-quinazolinedione

생성물 1

HCID 229233356-Amino-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline수율 63%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

In a solvent mixture of 15 ml of ethanol and 5 ml of water was dissolved 500 mg (1.02 mmol) of Compound 1 obtained in Example 1, and 500 mg of iron and a catalytic amount of ferric chloride were added thereto, followed by heating under reflux for 1 hour. The reaction mixture was filtered while hot by using a filter aid, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed and dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1) and recrystallized from ether to give 275.2 mg (yield: 63%) of Compound 14 as pale yellow crystals.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. filtrationThe reaction mixture was filtered while hot
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionextracted with chloroform
  7. washThe organic layer was washed
  8. customdried
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
  11. customrecrystallized from ether

출처 및 근거

ORD 기록
ord-8ed7530963bf4bd5ad6220f2b289d0ce
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05605900

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