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tert-butyl N-(pyrrolidin-3-yl)carbamate → 7-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid

HRID 364054
ノート
印刷プレビュー

反応式

HRID 364054 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([NH:14][CH3:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[NH:20]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]1>C(#N)C>[CH3:30][C:28]([CH3:31])([O:27][C:26]([NH:25][CH:22]1[CH2:23][CH2:24][N:20]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]3[NH:14][CH3:15])=[CH:3][C:2]=2[F:1])[CH2:21]1)=[O:32])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 135580371-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 705150537-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid収率 57.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To 1.00 g (3.68 mmol) of 6,7,8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid in 10 ml of acetonitrile was added 0.56 g (1.0 equivalent) of 1,8-diazobicyclo-[5,4,0]undec-7-ene and 0.68 g of 1,1-dimethylethyl 3-pyrrolidinylcarbamate. The mixture was refluxed for one hour and stirred at room temperature overnight. The solids were filtered and washed with ether to give 0.92 g of 7-[3-[[(1,1dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid. A portion of this material (0.38 g) was treated with 10 ml of trifluoroacetic acid for 2 hours and was concentrated. The residue was taken up in aqueous sodium hydroxide to pH 12.5 and then treated with hydrochloric acid to pH 7.0. The solids were filtered to give 0.24 g of 7-(3-amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, mp 210°-211° C.

後処理

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe solids were filtered
  3. washwashed with ether

出典と根拠

ORDレコード
ord-597dd3106fde4a2189a52777bbd0c6a2
出典データセット
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04604401

反応ノート

読み込み中…

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