(3S)-(-)-3-Aminopyrrolidine → (S)-tert-Butyl 2-(6-(3-aminopyrrolidin-1-yl)nicotinamido)phenylcarbamate

HRID 1661504

Reaktionsgleichung

Reaktionsgleichung von HRID 1661504
Cl[C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:7])=[CH:4][N:3]=1.[NH2:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>CS(C)=O.O>[NH2:25][C@H:26]1[CH2:30][CH2:29][N:28]([C:2]2[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:7])=[CH:4][N:3]=2)[CH2:27]1

Komponenten

5

Edukt 2

HCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 57717462tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate

Produkt 1

HCID 59806014(S)-tert-Butyl 2-(6-(3-aminopyrrolidin-1-yl)nicotinamido)phenylcarbamateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of compound 94 (1.00 g, 2.88 mmol) and 3-(S)(−)aminopyrrolidine (495 mg, 5.75 mmol) in DMSO (5 ml) was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature and stirred for an additional 16 h and diluted with water. The aqueous solution was extracted with AcOEt/dichloromethane mixture, washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound 153 as an orange solid (981 mg, 86% yield). 1H NMR: (DMSO) δ (ppm): 8.76 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 3.70-3.53 (m, 4H), 3.26 (dd, J=11.3, 3.9 Hz, 1H), 2.07-1.98 (m, 1H), 1.75-1.67 (m, 3H), 1.29 (t, J=7.0 Hz, 3H). LRMS (ESI): (calc.) 397.2; (obt.) 398.3 (M+H)+.

Aufarbeitung

  1. extractionThe aqueous solution was extracted with AcOEt/dichloromethane mixture
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7702d97dafc94810b94fd4e91396e363
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030344B2

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