Triethylamine → [5-(1-Isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 1786481ノート

反応式

HRID 1786481 の反応式
Cl.Cl.[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:16]3)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH:3]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22]([N:24]2[CH2:29][CH2:28][N:27]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:26][CH2:25]2)=[O:23])=[CH:16]3)[CH2:10][CH2:11]1)([CH3:5])[CH3:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68565070[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride

生成物 1

HCID 24958929[5-(1-Isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride (82 mg, 0.22 mmol) in dichloromethane (2 ml) were added triethylamine (4.2 eq, 0.13 ml) and methanesulfonyl chloride (1.4 eq, 0.02 ml). The mixture was stirred overnight, diluted with dichloromethane and washed with 1N aqueous sodium bicarbonate solution. The phases were separated, the aqueous phase extracted with dichloromethane, and the combined organic phases washed with brine and dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel (1:0 to 5:1 dichloromethane/methanol eluant) to afford the title compound as an off-white solid. MS (m/z): 449.2 (M+H)+.

後処理

  1. washwashed with 1N aqueous sodium bicarbonate solution
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with dichloromethane
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by column chromatography on silica gel (1:0 to 5:1 dichloromethane/methanol eluant)

出典と根拠

ORDレコード
ord-adfe3d9336b84d1ba1667c8e82b797e0
出典データセット
uspto-grants-2009_03
特許番号
US07507736B2

反応ノート

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