Sodium Iodide → (S)-2-(4-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)butyl)isoindoline-1,3-dione

HRID 2061627

Reaktionsgleichung

Reaktionsgleichung von HRID 2061627
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH3:25][CH2:26][CH2:27][NH:28][C@@H:29]1[CH2:38][C:33]2[S:34][C:35]([NH2:37])=[N:36][C:32]=2[CH2:31][CH2:30]1>C(#N)C>[NH2:37][C:35]1[S:34][C:33]2[CH2:38][C@@H:29]([N:28]([CH2:27][CH2:26][CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:7]3=[O:16])[CH2:30][CH2:31][C:32]=2[N:36]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 119570Pramipexole

Produkt 1

HCID 58369715(S)-2-(4-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)butyl)isoindoline-1,3-dioneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-(4-bromobutyl)-phthalimide (2.25 g, 7.98 mmol), cesium carbonate (2.6 g, 7.98 mmol), and sodium iodide (1.80 g, 12 mmol) were added to a solution of pramipexole 1 (1.53 g, 7.25 mmol) in acetonitrile (50 mL). After refluxing for 3 hours, the mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, and dried over anhydrous Na2SO4. Flash column chromatography (MeOH/EtOAc, 5:95) gave 13 as a colorless oil (2.7 g, 90.4%). 1H NMR (CDCl3, 300 MHz) δ 7.88-8.00 (m, 2H), 7.78-7.60 (m, 2H), 4.90 (s, 2H), 3.70 (t, J=7.2 Hz, 2H), 3.10-2.95 (m, 1H), 2.78-2.30 (m, 8H), 2.05-1.90 (m, 1H), 1.77-1.60 (m, 3H), 1.56-1.40 (m, 4H), 0.87 (t, J=7.2 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ168.89, 165.83, 145.53, 134.28, 132.53, 123.58, 117.96, 57.59, 52.97, 50.41, 38.34, 27.01, 26.81, 26.71, 26.05, 25.33, 22.64, 12.24.

Aufarbeitung

  1. temperatureAfter refluxing for 3 hours
  2. customthe mixture was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-9e5071c65577407b880d653653ca8104
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283368B2

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