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Triethylamine → 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid

HRID 561155
ノート
印刷プレビュー

反応式

HRID 561155 の反応式
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][CH2:36][CH2:37][NH2:38].C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O.O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:38][CH2:37][CH2:36][NH:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 590030445-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid

生成物 1

HCID 590029455-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid
収率 50%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A solution of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid (550 mg, 1.42 mmol), N-2-pyridyl-1,2-ethanediamine (292 mg, 2.13 mmol) and triethylamine (0.297 mL, 2.13 mmol) in DMSO (7 mL) was stirred at 120° C. for 6 h. To the reaction mixture, water and NH4Cl was added to neutralize and the suspension was stirred for 30 min. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 1:1→1:5) to yield 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (356 mg, 50%) as a yellow solid.

後処理

  1. extractionThe crude product was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography (Hexane:EtOAc 1:1→1:5)

出典と根拠

ORDレコード
ord-cbf9c7b543704a48aa1f0474aa8aea0c
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063221B2

反応ノート

読み込み中…

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