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

HRID 1786481노트

반응식

HRID 1786481 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-adfe3d9336b84d1ba1667c8e82b797e0
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507736B2

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