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 430588ノート

反応式

HRID 430588 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd94acd980a4433eb71afbd6680f6f58
出典データセット
uspto-grants-2001_11
特許番号
US06323213B1

反応ノート

読み込み中…