Potassium Carbonate → HCID 57961664, Verbindung

HRID 541836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541836
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:26][C:27]1[N:32]=[C:31](Cl)[C:30]([Cl:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:27]1[N:32]=[C:31]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:15]=[CH:16][CH:17]=3)=[O:10])[CH:5]=[CH:6][CH:7]=2)[C:30]([Cl:34])=[CH:29][N:28]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962170tert-Butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamate

Produkt 1

HCID 57961664HCID 57961664, VerbindungAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamate (0.31 g, 0.91 mmol) and 2,4,5-trichloropyrimidine (0.15 g, 0.82 mmol) in DMF (3 mL) was added potassium carbonate (0.14 g, 0.99 mmol). The resulting mixture was stirred overnight at rt. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous was extracted with EtOAc and the combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude mixture was purified by column chromatography to give the desired product (0.25 g, 62%). LCMS for C23H23Cl2N5O3 (M-tBu+H)+: m/z=432.0, 434.0. 1H NMR (400 MHz, DMSO-d6): δ 10.12 (s, 1H), 9.54 (s, 1H), 9.32 (s, 1H), 8.35 (s, 1H), 7.93 (s, 1H), 7.78 (t, J=2.1 Hz, 1H), 7.47 (s, 1H), 7.46 (m, 1H), 7.33 (dd, J=8.7, 7.5 Hz, 1H), 7.31 (m, 1H), 7.15 (m, 1H), 7.11 (t, J=8.0 Hz, 1H), 6.98 (m, 1H).

Aufarbeitung

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous was extracted with EtOAc
  5. washthe combined organics were washed with water and brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21db813c8bd045218096412aab4330a8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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