Sodium Carbonate → (E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

HRID 333949ノート

反応式

HRID 333949 の反応式
O[CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6].C(N(S(F)(F)[F:31])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:31][CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2 回HCID 86691596(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

生成物 1

HCID 56949080(E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (32.5 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (200 μl) and added to a solution of (diethylamino)sulphur trifluoride (DAST; 19 μl, 0.12 mmol) in 200 μl dichloromethane. The mixture was stirred for 30 minutes at room temperature, additional DAST was added (10 μl, 0.063 mmol) and stirring was continued for additional 30 minutes. Solid sodium carbonate (25 mg) was added, the mixture was filtered, the filtrate evaporated to dryness and the residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 4 mg (0.012 mmol, 12%).

後処理

  1. stirringstirring
  2. waitwas continued for additional 30 minutes
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customthe residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  6. customto yield 4 mg (0.012 mmol, 12%)

出典と根拠

ORDレコード
ord-6bf75af861a74a5d9256c2e2ffcf0118
出典データセット
uspto-grants-2014_11
特許番号
US08883791B2

反応ノート

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