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

Reaktionsgleichung

Reaktionsgleichung von HRID 453920
[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

Komponenten

7

Edukt 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

Produkt 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)benzenesulfonamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-006d998348344de28b4803f8c76b3f2b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492559B2

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