Succinic anhydride → 1-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]pyrrolidine-2,5-dione

HRID 885975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885975
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[C:24]1(=O)[O:29][C:27](=[O:28])[CH2:26][CH2:25]1>CN(C=O)C>[CH3:20][C:16]1([CH3:21])[NH:15][C:14](=[O:22])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([N:1]5[C:27](=[O:28])[CH2:26][CH2:25][C:24]5=[O:29])[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1

Komponenten

4

Edukt 2

HCID 7922Succinic anhydrideHCID 584416902-(6-amino-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydro-6,6-dimethylthiazolo[5,4-c]pyridin-4(5H)-one

Produkt 1

HCID 671861051-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]pyrrolidine-2,5-dioneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of Example 42 (50 mg, 0.15 mmol) and succinic anhydride (20 mg, 0.15 mmol) in DMF (4 mL) was stirred at 140° C. under microwave irradiation for 1 h. The reaction mixture was concentrated in vacuo, dissolved in acetic acid and stirred at 140° C. under microwave irradiation for 1 h. It was concentrated in vacuo and purified by preparative HPLC (Method 7) to give the title compound (21 mg, 34%) as an off-white solid. δH (CDCl3) 8.05 (1H, d, J 2.1 Hz), 7.11-6.91 (2H, m), 5.45 (1H, s), 4.41-4.32 (2H, m), 4.19-4.10 (2H, m), 2.92 (4H, s), 2.88 (2H, s), 1.39 (6H, s). LCMS (ES+) 413.0 (M+H)+, RT 2.58 minutes (Method 2).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in acetic acid
  3. concentrationIt was concentrated in vacuo
  4. custompurified by preparative HPLC (Method 7)

Quellen und Nachweise

ORD-Eintrag
ord-f0a5a4ed4f5748e6bd10dfb6dbf3a57b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242116B2

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