1,1'-Carbonyldiimidazole → HCID 53476700, Verbindung

HRID 1505223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505223
[CH3:1][O:2][C:3]1[C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=[C:5]([C:11]([F:14])([F:13])[F:12])[N:4]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1.[NH2:27][C:28]1[C:33]2[O:34][CH2:35][C:36](=[O:38])[NH:37][C:32]=2[CH:31]=[CH:30][CH:29]=1>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][NH:10][C:20]([NH:27][C:28]2[C:33]3[O:34][CH2:35][C:36](=[O:38])[NH:37][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:21])=[CH:7][CH:6]=[C:5]([C:11]([F:14])([F:12])[F:13])[N:4]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-oneHCID 58873546(2-methoxy-6-(trifluoromethyl)pyridin-3-yl)methanamine

Produkt 1

HCID 53476700HCID 53476700, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 29c (0.38 g, 1.84 mmol) in THF (15 mL) was added CDI (2.1 mol eq, 0.63 g) and the mixture was heated at 70° C. overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×25 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (yellow oil, 0.62 g, quantitative yield). The oil obtained was dissolved in DMF (20 mL) and the bicyclic amine 1f was added (0.8 mol eq, 0.21 g), then the mixture obtained was heated at 100° C. overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (1:1 EtOAc:petroleum ether) to afford the product as a white solid (0.1 g, 14% Yield). 1HNMR (DMSO, 400 MHz) δ 3.96 (s, 3H), 4.29 (d, 2H, J=6), 4.62 (s, 2H), 6.46 (dd, 1H, J=2), 6.80 (t, 1H, J=8), 7.34 (bt, 1H), 7.51 (d, 1H, J=8), 7.72 (m, 2H), 8.24 (s, 1H), 10.66 (s, 1H). [M+1] 396.99 (C17H15F3N4O4 requires 396.32).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with EtOAc (3×25 mL)
  4. customevaporated at reduced pressure (yellow oil, 0.62 g, quantitative yield)
  5. customThe oil obtained
  6. custom0.21 g), then the mixture obtained
  7. temperaturewas heated at 100° C. overnight
  8. customThe solvent was removed at reduced pressure
  9. customthe residue was purified by chromatography (1:1 EtOAc:petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-1f829a884f3740e78654108ef466bcb1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216975B2

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