Potassium Carbonate → 1-(Cyclohexanecarbonyl)indoline-5-sulfonamide

HRID 528823

Reaktionsgleichung

Reaktionsgleichung von HRID 528823
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:14]1([C:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×

Produkt 1

HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamideAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of indoline-5-sulfonamide (Intermediate 54A, 100 mg, 0.50 mmol) in MeCN (5.0 mL) was added cyclohexanecarbonyl chloride (0.14 mL, 1.00 mmol) and K2CO3 (174 mg, 1.26 mmol). The resulting reaction mixture was stirred at room temperature overnight and then diluted with EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with 1 N aq. NaOH solution, followed by 10% aq. LiCl solution. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the title compound (31 mg, 20%) as a white solid. 1H NMR (DMSO-d6) δ 8.16 (d, J=6.8 Hz, 1H), 7.64-7.60 (m, 2H), 7.19 (m, 2H), 4.22 (t, J=8.5 Hz, 2H), 3.21-3.16 (m, 2H), 2.62-2.55 (m, 1H), 1.91-1.65 (m, 5H), 1.45-1.16 (m, 5H); MS(ESI+) m/z 309.1 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with 1 N aq. NaOH solution
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-1a274eb274754d368c893024268328f8
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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