1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(3-Trifluoroacetylamino-1-pyrrolidinyl)-1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid

HRID 1031557ノート

反応式

HRID 1031557 の反応式
[CH3:1][C:2]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:16])=[C:12](F)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]1)([CH3:4])[CH3:3].Cl.[F:22][C:23]([F:33])([F:32])[C:24]([NH:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)=[O:25].N12CCCN=C1CCCCC2>N1C=CC=CC=1>[F:33][C:23]([F:22])([F:32])[C:24]([NH:26][CH:27]1[CH2:31][CH2:30][N:29]([C:12]2[CH:13]=[C:14]3[C:9]([C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6][N:5]3[C:2]([CH3:4])([CH3:1])[CH3:3])=[CH:10][C:11]=2[F:16])[CH2:28]1)=[O:25]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27606983-(Trifluoroacetamido)pyrrolidine HydrochlorideHCID 148395931-(1,1-Dimethylethyl)-1,4-dihydro-6,7-difluoro-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 148395997-(3-Trifluoroacetylamino-1-pyrrolidinyl)-1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid収率 45.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 600 mg (2.13 mmoles) 1-(1,1-dimethylethyl)-1,4-dihydro-6,7-difluoro-4-oxo-3-quinolinecarboxylic acid, 700 mg (3.2 mmoles) of 3-trifluoroacetylamino pyrrolidine hydrochloride and 1.3 mL (8.5 mmoles) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 3 mL pyridine was stirred 30 minutes at room temperature, evaporated to dryness and poured into water. The pH was adjusted to 7.5 with 1N hydrochloric acid. The precipitate was filtered to give 430 mg of 7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid. mp 200° C. dec. 409 mg (0.92 mmole) of that compound was suspended in 2 mL 1N NaOH and refluxed 2 hours. The solution was cooled and diluted with water, the pH was adjusted to 7.5 with 10% acetic acid. The precipitate was filtered, washed with water, dried and recrystallized as an hydrochloride in ethanol to give 180 mg of titled compound. MP>270° C.

後処理

  1. customevaporated to dryness
  2. additionpoured into water
  3. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-5e454399d5fb4c78afc2bd16f90d380d
出典データセット
uspto-grants-1990_09
特許番号
US04954507

反応ノート

読み込み中…