Potassium Carbonate → methyl 2-(5,5-dimethyl-5'-(N-(2-morpholinoethyl)-methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

HRID 571325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571325
[CH3:1][C:2]1([CH3:27])[CH2:26][O:25][C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=3)[N:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:6]2=[O:24])[O:4][CH2:3]1.Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1([CH3:27])[CH2:3][O:4][C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N:14]([CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=3)[N:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:6]2=[O:24])[O:25][CH2:26]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86681649Methyl 2-(5,5-dimethyl-5'-(methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

Produkt 1

HCID 86681740methyl 2-(5,5-dimethyl-5'-(N-(2-morpholinoethyl)-methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of methyl 2-(5,5-dimethyl-5′-(methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.400 g, 1.004 mmol), 4-(2-chloroethyl)morpholine hydrochloride (0.224 g, 1.204 mmol) (prepared in an analogous manner as described in Example 17, Scheme 17, Steps 1, 2, 3, 4) and K2CO3 (0.306 g, 2.208 mmol) in DMF (8 ml) was heated at 70° C. for 3 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed several times with brine and dried over sodium sulfate; the solvent was removed and the crude was purified by chromatography on silica gel cartridge (DCM:MeOH=99:1 to 97:3) affording methyl 2-(5,5-dimethyl-5′-(N-(2-morpholinoethyl)-methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.453 g, 0.885 mmol, 88% yield, MS/ESI+ 512.1 [MH]+).

Aufarbeitung

  1. customprepared in an analogous manner
  2. customThe mixture was partitioned between ethyl acetate and water
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed several times with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. customthe crude was purified by chromatography on silica gel cartridge (DCM:MeOH=99:1 to 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-a332736939044158985a23ed82597019
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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