Sodium Bicarbonate → 4-Methoxy-2,6-dimethyl-N-((1-(2-oxo-2-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethyl)-1H-indol-7-yl)methyl)benzenesulfonamide

HRID 453920

반응식

HRID 453920 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]3([CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)[CH2:17][CH2:16]1)=[O:14])[CH:9]=[CH:8]2.C([O-])(O)=O.[Na+].[CH3:37][C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([CH3:46])[C:39]=1[S:47](Cl)(=[O:49])=[O:48]>C1COCC1.O.C1COCC1.O>[CH3:45][O:44][C:42]1[CH:43]=[C:38]([CH3:37])[C:39]([S:47]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]3[C:11]=2[N:10]([CH2:12][C:13](=[O:14])[N:15]2[CH2:20][CH2:19][C:18]4([CH2:21][CH2:22][N:23]([C:26]5[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=5)[CH2:24][CH2:25]4)[CH2:17][CH2:16]2)[CH:9]=[CH:8]3)(=[O:48])=[O:49])=[C:40]([CH3:46])[CH:41]=1

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 594736752-(7-(aminomethyl)-1H-indol-1-yl)-1-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethanone

생성물 1

HCID 468969494-Methoxy-2,6-dimethyl-N-((1-(2-oxo-2-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethyl)-1H-indol-7-yl)methyl)benzenesulfonamide수율 38%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

A mixture of 2-(7-(aminomethyl)-1H-indol-1-yl)-1-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethanone (220 mg, 0.53 mmol, 1.0 equiv.) and NaHCO3 (134 mg, 1.59 mmol, 3.0 equiv.) in THF-water(1:1, 20 ml) was added at 0° C. to a solution of 2,6-dimethyl-4-methoxyphenylsulfonyl chloride (136 mg, 0.58 mmol, 1.1 equiv.) in THF (5 ml), and the mixture was stirred for 16 h at RT. The reaction mixture was diluted with water (15 ml) and extracted with ethyl acetate (3×30 ml). The combined organic phases were washed with sat. NaCl solution (40 ml) and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by column chromatography (silica gel; 6-8% MeOH/DCM), and the desired product was thus obtained in the form of a white solid.

후처리

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe combined organic phases were washed with sat. NaCl solution (40 ml)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe crude product was purified by column chromatography (silica gel; 6-8% MeOH/DCM)

출처 및 근거

ORD 기록
ord-006d998348344de28b4803f8c76b3f2b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492559B2

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