Dabco → Methyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 651282노트

반응식

HRID 651282 반응식
[C:1]([C:3]1[C:4](Cl)=[C:5]([F:21])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]2=[O:20])#[N:2].[C@@H:23]12[CH2:31][NH:30][CH2:29][C@@H:28]1[CH2:27][CH2:26][CH2:25][NH:24]2.N12CCN(CC1)CC2>C(#N)C>[C:1]([C:3]1[C:4]([N:30]2[CH2:31][C@@H:23]3[C@@H:28]([CH2:27][CH2:26][CH2:25][NH:24]3)[CH2:29]2)=[C:5]([F:21])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]2=[O:20])#[N:2]

참가 물질

5

반응물 3

HCID 9237DabcoHCID 10313138(1S,6S)-2,8-Diazabicyclo(4.3.0)nonaneHCID 18351232Methyl 8-cyano-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

생성물 1

HCID 15347199Methyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

200 mg (0.625 mmol) of methyl 8-cyano-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 86 mg (0.683 mmol) of (1S,6S)-2,8-diazabicyclo[4.3.0]nonane and 150 mg (1.34 mmol) of 1,4-diazabicyclo[2.2.2]-octane are stirred in 6 ml of acetonitrile at room temperature for 48 hours. Thereafter, the mixture is evaporated and the residue is partitioned between 15 ml of chloroform and 20 ml of saturated sodium carbonate solution. The organic phase is separated off, the aqueous phase is extracted again with chloroform and, after drying with sodium sulfate, the combined extracts are evaporated. For purification, the residue is chromatographed over silica gel with ethyl acetate/ethanol/25% strength aqueous ammonia solution.

후처리

  1. customThereafter, the mixture is evaporated
  2. customthe residue is partitioned between 15 ml of chloroform and 20 ml of saturated sodium carbonate solution
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted again with chloroform
  5. dry with materialafter drying with sodium sulfate
  6. customthe combined extracts are evaporated
  7. customFor purification
  8. customthe residue is chromatographed over silica gel with ethyl acetate/ethanol/25% strength aqueous ammonia solution

출처 및 근거

ORD 기록
ord-54db9c0c21304d0d8e3aff2fba0042cc
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06278013B1

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