1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534820노트

반응식

HRID 1534820 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:21]12[CH2:28][NH:27][CH2:26][C:25]=1[CH2:24][NH:23][CH2:22]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:23]4[CH2:24][C:25]5[CH2:26][NH:27][CH2:28][C:21]=5[CH2:22]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 151922531,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole

생성물 1

HCID 98643051-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid수율 81.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

0.28 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.16 g of 3,7-diazabicyclo-[3.3.0]oct-1(5)-ene and 0.3 ml of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) were suspended in 20 ml of acetonitrile and refluxed in 100° C. oil bath for 5 hours. The reaction mixture was kept overnight at room temperature. The produced precipitate was filtered and was washed with ethanol-ethylether (1:1) solvent. 0.3 g of the title compound was obtained (yield 80%).

후처리

  1. filtrationThe produced precipitate was filtered
  2. washwas washed with ethanol-ethylether (1:1) solvent

출처 및 근거

ORD 기록
ord-ffc4b9d0df8849658f70f7cd765927d1
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05091384

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