Triethylamine → 5-Amino-7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

HRID 2372091ノート

反応式

HRID 2372091 の反応式
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.C(OC([NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:32]2[CH2:33][CH2:34][CH:30]([NH2:29])[CH2:31]2)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 148965465-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

生成物 1

HCID 30259245-Amino-7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid収率 63%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To 1.57 g (5 mmol) of 5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid in 20 ml of acetonitrile was added 0.93 g (5 mmol) of 3-[(t-butoxycarbonyl)amino]pyrrolidine and 1.0 g (10 mmol) of triethylamine. The mixture was refluxed for three hours, cooled, and filtered. The solids were washed with acetonitrile and ether, then dissolved in 10 ml of acetic acid and 2 ml of 3N hydrochloric acid. The mixture was heated at 100° C. for four hours, concentrated, and triturated with 2-propanol. The solid that formed was filtered and washed with ether to give 1.2 g of the title compound.

後処理

  1. temperatureThe mixture was refluxed for three hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solids were washed with acetonitrile and ether
  5. dissolutiondissolved in 10 ml of acetic acid
  6. concentrationconcentrated
  7. customtriturated with 2-propanol
  8. customThe solid that formed
  9. filtrationwas filtered
  10. washwashed with ether

出典と根拠

ORDレコード
ord-153c9fb6beec489fa264318e404b3416
出典データセット
uspto-grants-1992_03
特許番号
US05097032

反応ノート

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