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Water → 3-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline

HRID 1451919
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HRID 1451919 반응식
Br.[N+:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[N:9]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:8]2=[O:22])([O-:4])=[O:3].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:35][O:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:36][CH3:37])[N:27]=[CH:26][N:25]=[C:24]2[N:19]1[CH2:18][CH2:17][CH:16]([N:9]2[C:8](=[O:22])[C:7]3[C:12](=[CH:13][CH:14]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=3)[NH:11][C:10]2=[O:15])[CH2:21][CH2:20]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 229235601,2,3,4-Tetrahydro-6-nitro-2,4-dioxo-3-(4-piperidinyl)-quinazoline hydrobromide

생성물 1

HCID 229233993-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

In 150 ml of DMF was dissolved 3.0 g (8.09 mmol) of 1,2,3,4-tetrahydro-6-nitro-2, 4-dioxo-3-(4-piperidinyl)quinazoline hydrobromide, and 1.7 g (8.09 mmol) of 4-chloro6,7-dimethoxyquinazoline and 1.1 g (24 mmol) of potassium carbonate were added to the solution, followed by heating at 80° C. for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with an aqueous solution of sodium chloride and dried. After the solvent was distilled off, ethanol and ether were added to the residue. The precipitated crystals were collected by filtration and washed with ether to give 3.28 g (yield: 8=%) of Compound 24 as white crystals 1H-HMR (DMSO-d6) δ (ppm) 12.01 (s, 1H, NH), 8.67 (d, 1H, J=2.5 Hz), 8.55 (s, 1H), 8.45 (dd, 1H, J=9.0, 2.5 Hz), 7.34 (d, 1H, J=9.0 Hz), 7.23 (s, 1H), 7.15 (s, 1H), 5.09-5.04 (m, 1H), 4.37-4.32 (br.-d, 2H), 3.95 (s, 3H), 3.93 (s, 3H), 3.27-3.23 (br.-t, 2H), 2.87-2.78 (m, 2H), 1.81-1.77 (br.-d, 2H).

후처리

  1. additionwere added to the solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with an aqueous solution of sodium chloride
  4. customdried
  5. distillationAfter the solvent was distilled off
  6. additionethanol and ether were added to the residue
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with ether

출처 및 근거

ORD 기록
ord-ba4b643664b24b73bfd4c7c5f3663c7b
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05605900

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