Sodium Iodide → Tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 2362969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362969
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].Cl[CH2:33][CH2:34][CH2:35][N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([CH3:46])([CH3:45])[C:37]1=[O:47].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:46][C:38]1([CH3:45])[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:36]([CH2:35][CH2:34][CH2:33][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)[C:37]1=[O:47]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateHCID 580466771-(3-Chloropropyl)-3,3-dimethylindolin-2-one

Produkt 1

HCID 58046720Tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
81 °C

Versuchsvorschrift

A mixture of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (300 mg, 0.71 mmol, 1 equiv), 1-(3-chloropropyl)-3,3-dimethylindolin-2-one (200.8 mg, 0.71 mmol, 1 equiv), sodium iodide (42.7 mg, 0.285 mmol, 0.4 equiv), and potassium carbonate (295.2 mg, 2.136 mmol, 3 equiv) in 2-butanone was stirred at 81° C. for 16 h. After cooling the reaction mixture, the crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the crude residue was purified using preparatory thin layer chromatography in 5% methanol in dichloromethane to afford the title compound as cream crystals (210 mg, 47.4%); 1H NMR (400 MHz, DMSO-d6): δ 1.27 (s, 6H); 1.52 (s, 9H); 1.63 (d, 2H, J=12.4 Hz); 1.79 (bs, 2H); 2.36 (bs, 2H); 2.52-2.59 (m, 2H); 2.66-2.73 (m, 4H); 3.75 (t, 2H, J=6.8 Hz); 4.59 (s, 2H); 4.61 (s, 2H); 6.77 (t, 1H, J=6.8 and 7.2 Hz); 6.85 (d, 2H, J=8.4 Hz); 7.03 (t, 1H, J=7.6 and 6.8 Hz); 7.13 (d, 1H, J=7.6 Hz); 7.23 (t, 3H, J=8 and 7.6 Hz); 7.35 (d, 1H, J=7.2 Hz); 7.48-7.55 (m, 2H); 7.79 (s, 1H); 7.82-7.84 (m, 1H); MS for C38H46N4O4 m/z 623.18 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. customthe crude mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-41bff00cd3cc4362b021cce653054496
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691836B2

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