1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(3-{1-[(1-tert-Butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 1292850ノート

反応式

HRID 1292850 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:23])[C:15]2([CH:18]3[CH2:22][CH2:21][NH:20][CH2:19]3)[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:40])=[C:34](F)[C:35]=3[O:37][CH3:38])[C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28]2)[CH2:26][CH2:25]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:23])[C:15]2([CH:18]3[CH2:22][CH2:21][N:20]([C:34]4[C:35]([O:37][CH3:38])=[C:36]5[C:31]([C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28][N:27]5[CH:24]5[CH2:26][CH2:25]5)=[CH:32][C:33]=4[F:40])[CH2:19]3)[CH2:16][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 688921244-[Methyl-(1-pyrrolidin-3-yl-cyclopropyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 694924817-(3-{1-[(1-tert-Butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

A solution of 4-[methyl-(1-pyrrolidin-3-yl-cyclopropyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.31 mmol) in acetonitrile (30.0 mL) was added 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (98 mg, 0.33 mmol) and DBU (0.23 mL, 1.53 mmol). The suspension was heated to 75° C. overnight. The reaction mixture was partitioned between ethyl acetate and 5% citric acid. The separated organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (10% methanol in dichloromethane) to give the title compound as a yellow solid (102 mg, 62%). ESI MS m/z 599.3 (M+H+).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and 5% citric acid
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-e43a46d6cfdc4ceb9aae55033b96b456
出典データセット
uspto-grants-2007_07
特許番号
US07238694B2

反応ノート

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