Ammonium Chloride → 7-[2-(3-Diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acid

HRID 1778326ノート

反応式

HRID 1778326 の反応式
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:27]([C:28]([O:30]C)=[O:29])=[C:26]2[C:21]([C:22]3[CH:34]=[CH:33][O:32][C:23]=3[CH:24]=[N:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].O.[OH-].[Li+].[Cl-].[NH4+]>O1CCOCC1.O>[CH2:35]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:27]([C:28]([OH:30])=[O:29])=[C:26]2[C:21]([C:22]3[CH:34]=[CH:33][O:32][C:23]=3[CH:24]=[N:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:36]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 66685060Methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate2 回

生成物 1

HCID 566562807-[2-(3-Diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acid収率 46.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate (Intermediate 71, 0.100 g) and lithium hydroxide monohydrate (0.250 g) in dioxane (4 mL) and water (1.25 mL) was heated at 80° C. overnight. The mixture was cooled and saturated aqueous ammonium chloride was added. This was concentrated in vacuo and the residue was triturated with DCM and methanol, filtered and the filtrate was concentrated in vacuo. The residue was purified by HPLC (C6 Ph) eluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 10-40% to give a yellow gum. The product was triturated with ether to give 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acid (0.045 g) as a yellow solid.

後処理

  1. temperatureThe mixture was cooled
  2. concentrationThis was concentrated in vacuo
  3. customthe residue was triturated with DCM and methanol
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by HPLC (C6 Ph)
  7. washeluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 10-40%
  8. customto give a yellow gum
  9. customThe product was triturated with ether

出典と根拠

ORDレコード
ord-d4cff78819d04bbcbb38cf2bb42ab2ed
出典データセット
uspto-grants-2016_02
特許番号
US09266896B2

反応ノート

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