Water → HCID 178486910, Verbindung

HRID 1295739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295739
[CH3:1][S:2]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[CH2:9][NH:10][CH3:11])=[O:3].Cl[C:16]1[NH:17][C:18]2[C:23]([C:24](=[O:26])[N:25]=1)=[C:22]([CH3:27])[C:21]([O:28][CH3:29])=[C:20]([O:30][CH3:31])[CH:19]=2.CCN(CC)CC.O>CS(C)=O>[CH3:1][S:2]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[CH2:9][N:10]([CH3:11])[C:16]1[NH:17][C:18]2[C:23]([C:24](=[O:26])[N:25]=1)=[C:22]([CH3:27])[C:21]([O:28][CH3:29])=[C:20]([O:30][CH3:31])[CH:19]=2)=[O:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 69508634HCID 69508634, VerbindungHCID 178486897HCID 178486897, Verbindung

Produkt 1

HCID 178486910HCID 178486910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Compound from step 4 (213 mg, 1.00 mmol) and 2-chloro-6,7-dimethoxy-5-methyl-1H-quinazolin-4-one (254 mg, 1.00 mmol) were dissolved in dry DMSO. Et3N (0.14 mL, 1.00 mmol) was added, and the mixture was heated to 120° C. overnight. Upon cooling, the mixture was poured into water and extracted with diethyl ether. The ethereal extracts were dried over Na2SO4 and concentrated in vacuo. The residue was recrystallized from MeOH to give 54 mg (12.53%) of the above Example F-2 as a white crystalline powder. mp 191.0–193.5° C.; 1H NMR (DMSO-d6, 2.49) δ 2.59 (s, 3 H), 2.60 (s, 3 H), 3.03 (s, 3 H), 3.62 (s, 3 H), 3.84 (s, 3 H), 4.79 (s, 2 H), 5.02 (d, 1 H, J=10.6), 5.22 (d, 1 H, J=10.6), 6.64 (s, 1 H), 6.90 (d, 1 H, J=7.6), 7.01 (m, 2 H), 7.30 (t, 1 H, J=7.9); 13C NMR (DMSO-d6, 39.50) δ 13.90, 34.66, 35.59, 51.90, 55.93, 60.23, 84.92, 104.81, 108.46, 114.18, 115.02, 121.22, 130.13, 131.94, 140.10, 142.90, 150.63, 150.97, 157.71, 157.97, 163.67; MS (ES+) m/z 432 (M+H); Anal. (C21H25N3O5S)C: calcd, 58.45; found, 58.32; H: calcd, 5.84; found, 5.74; N: calcd, 9.74; found, 9.77.

Aufarbeitung

  1. temperatureUpon cooling
  2. extractionextracted with diethyl ether
  3. dry with materialThe ethereal extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from MeOH
  6. customto give 54 mg (12.53%) of the above Example F-2 as a white crystalline powder

Quellen und Nachweise

ORD-Eintrag
ord-73e390abf8a445829d0ce5f97a5525b4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244738B2

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