Propanal → 2-methyl-4-[4-[(E)-pent-1-enyl]sulfonylpiperazin-1-yl]quinoline

HRID 333934ノート

反応式

HRID 333934 の反応式
C(OP([CH2:9][S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])(OCC)=O)C.[Br-].[Li+].C(=O)CC.[CH2:36]1[CH2:46]CN2C(=NCCC2)[CH2:38][CH2:37]1>C1COCC1.ClCCl>[CH3:29][C:21]1[CH:20]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([S:10](/[CH:9]=[CH:46]/[CH2:36][CH2:37][CH3:38])(=[O:12])=[O:11])[CH2:18][CH2:17]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

参加物

7

反応物 4

HCID 527PropanalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82050Lithium BromideHCID 866915914-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline

生成物 1

HCID 569489642-methyl-4-[4-[(E)-pent-1-enyl]sulfonylpiperazin-1-yl]quinoline収率 13.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline (47 mg, 0.106 mmol) was dissolved in anhydrous THF (1 ml), lithium bromide (11.1 mg, 0.128 mmol) and propionaldehyde (9.2 μl, 0.128 mmol) were added with stirring and the mixture was cooled to −10° C. DBU (15.2 μl, 0.102 mmol) was added, and the temperature was raised to room temperature. Stirring was continued for 30 minutes, the reaction mixture was diluted with dichloromethane, washed with 5% sodium bicarbonate solution (2×), water and evaporated to dryness. The residue was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile). 5 mg of a solid were obtained (0.014 mmol, 14%).

後処理

  1. temperaturethe temperature was raised to room temperature
  2. stirringStirring
  3. washwashed with 5% sodium bicarbonate solution (2×), water
  4. customevaporated to dryness
  5. customThe residue was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

出典と根拠

ORDレコード
ord-fcc0a5ed81fd48d980d45a3625a6b33a
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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