1,2-Dichloroethane → HCID 9892498, Verbindung

HRID 2220109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220109
C[N:2]1[C:9](=O)[CH2:8][C:6](=[O:7])N(C)C1=O.[NH2:12][C:13]1[CH:36]=[CH:35][C:16]([C:17]([NH:19][CH:20]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[C:28](O)=[O:29])=[O:22])=[O:18])=[CH:15][C:14]=1[Cl:37].C(N(C(C)C)CC)(C)C.C(Cl)CCl.[CH3:51][CH2:52][O:53][C:54](C)=[O:55]>C(Cl)Cl.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:52]([O:53][CH:54]1[CH:9]([NH:2][C:28]([CH:24]2[CH2:25][CH2:26][CH2:27][N:23]2[C:21](=[O:22])[CH:20]([NH:19][C:17](=[O:18])[C:16]2[CH:35]=[CH:36][C:13]([NH2:12])=[C:14]([Cl:37])[CH:15]=2)[C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:8][C:6](=[O:7])[O:55]1)[CH3:51]

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 69860Dimethylbarbituric acidHCID 81531DiisopropylethylamineHCID 10156704VX-765

Produkt 1

HCID 9892498HCID 9892498, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6 (5.05 g, 22.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added 1,3-dimethylbarbituric acid (DMBA) (3.78 g, 24.2 mmol)and Pd(PPh3)4 (0.15 g, 0.13 mmol) After 10 minutes, a solution of 5 (8.40 g, 22.0 mmol) in DMF (25 mL) was added followed by diisopropylethylamine (DIPEA) (7.66 mL, 44.1 mmol), (2.98 g, 22.0 mmol) and EDC (5.06 g, 26.4 mmol). The solution was stirred at 0° C. for 10 minutes then at room temperature for 18 hours. The reaction was diluted with EtOAc (200 mL), washed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL), dried over anhydrous MgSO4, and evaporated to dryness. Flash column chromatography on silica gel using CH2Cl2/MeOH, (99/1 to 98/2%) afforded the title compound as a white solid (11.20 g, 77% yield): 1H-NMR (500 MHz, CDCl3) δ1.08 (s, 9H), 1.27 (t, 3H), 1.85–1.99 (m, 1H), 2.00–2.06 (m. 1H), 2.07–2.18 (m, 1H), 2.32–2.48 (m, 2H), 2.78–2.89 (m, 1H), 3.62–3.76 (m, 2H), 3.82–3.96 (m, 2H), 4.39 (s, 1H), 4.54–4.60 (m, 1H), 4.62–4.76 (m, 1H), 4.85 (d, 1H), 6.57 (d, 1H), 6.73 (d, 1H), 7.38 (d, 1H), 7.49 (d, 1H), 7.72 (s, 1H). Analytical HPLC (cyano column): 13.10 min. LC-MS (ES+) m/e=509.4 (M+H), m.p.=96–99 ° C.

Aufarbeitung

  1. waitat room temperature for 18 hours
  2. washwashed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d36a7cd1659745388ba6f7a58aa52967
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417029B2

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