1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580589ノート

反応式

HRID 580589 の反応式
[Cl:1][C:2]1[C:3](F)=[C:4]([F:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH3:13])[CH:9]=[C:8]([C:14]([OH:16])=[O:15])[C:7]2=[O:17].C(OC([NH:27][C@H:28]1[C@@H:32]([CH3:33])[CH2:31][NH:30][CH2:29]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:27][C@H:28]1[C@@H:32]([CH3:33])[CH2:31][N:30]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:17])[C:8]([C:14]([OH:16])=[O:15])=[CH:9][N:10]3[CH2:12][CH3:13])=[CH:5][C:4]=2[F:18])[CH2:29]1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidineHCID 127708958-Chloro-1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 704197137-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 31.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 8-chloro-1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.25 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.21 g), DBU (0.15 g) and anhydrous acetonitrile (4 ml) was refluxed for 2.5 hours. Then, the reacting mixture was treated as described in example 22 to give the title compound (0.1 g) as white powder, mp 222°-224° C. (decompd.).

後処理

  1. temperaturewas refluxed for 2.5 hours
  2. additionThen, the reacting mixture was treated

出典と根拠

ORDレコード
ord-b6c87eb13d2a4694ae17c2898b584fb1
出典データセット
uspto-grants-1988_06
特許番号
US04753953

反応ノート

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