Iodoethane → 3-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione

HRID 2416855노트

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HRID 2416855 반응식
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([F:23])[C:14](F)=[C:15]([F:21])[C:16]=2[F:20])[NH:11][C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.[CH2:30](I)[CH3:31].[H-].[Na+]>CC(N(C)C)=O.CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([F:23])[C:14]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:15]([F:21])[C:16]=2[F:20])[N:11]([CH2:30][CH3:31])[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 226328803-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione

생성물 1

HCID 226329973-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione수율 22.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 31374Dimethylacetamide용매

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온도
60 °C

실험 절차

A solution of 3-benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione (Example W-3, 0.90 g, 2.7 mmol), in DMA (10 mL) was reacted with pyrrolidine (0.55 mL, 6.6 mmol) and heated to 60° C. for 3 hours. The mixture was then cooled and quenched with H2O and acidified with citric acid. The mixture was then extracted with ethyl acetate, dried with MgSO4, and concentrated. The residue was triturated with diethyl ether/hexanes and the solid filtered and dried (0.87 g). A portion of the solid (0.500 g, 1.28 mmol) was dissolved in DMF and reacted with ethyl iodide (1.0 mL, 12.77 mmol) and sodium hydride (0.060 g, 1.5 mmol). The mixture was stirred for 16 hours. The mixture was quenched with H2O and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate. and concentrated. The residue was triturated with diethyl ether and filtered to yield 0.25 g of the title compound as a solid.

후처리

  1. temperatureThe mixture was then cooled
  2. customquenched with H2O
  3. extractionThe mixture was then extracted with ethyl acetate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether/hexanes
  7. filtrationthe solid filtered
  8. customdried (0.87 g)
  9. customThe mixture was quenched with H2O
  10. extractionextracted with ethyl acetate
  11. dry with materialdried with sodium sulfate
  12. concentrationand concentrated
  13. customThe residue was triturated with diethyl ether
  14. filtrationfiltered

출처 및 근거

ORD 기록
ord-3dacb974c1d545168bd9b2aa9a893a08
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825199B2

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