Potassium Carbonate → HCID 57816823, Verbindung

HRID 2197477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197477
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH2:15])[N:7]=1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31]>CN(C=O)C>[NH2:15][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[CH2:23][C:24]1[CH:25]=[C:26]([CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31])[CH:34]=[CH:35][CH:36]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 57816773HCID 57816773, VerbindungHCID 178448875HCID 178448875, Verbindung

Produkt 1

HCID 57816823HCID 57816823, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 64 (300.0 mg, 1.45 mmol) and K2CO3 (200.0 mg, 1.45 mmol) was dissolved in DMF (5 mL) and to it was added 65 (420.0 mg, 1.45 mmol). The mixture was left to stir over night at room temperature, solvent was evaporated by rotary evaporation. The remaining solid was taken up in water and the product extracted with DCM (3×50 mL). Combined organic layers were washed with water (1×50 mL) and brine (2×50 mL) and dried over Na2SO4. Product was purified by flash column eluting 0-20% methanol in ethyl acetate to give 299.4 mg (50%) 66 as a solid. 1H NMR (300 MHz, CDCl3) δ 0.818 (t, 3H), 1.15 (t, 3H), 1.24 (d, 3H), 1.27 (m, 2H), 1.43 (m, 2H), 2.99 (d, 2H), 3.28 (m, 2H), 3.87 (m, 2H), 4.01 (m, 2H), 5.09 (s, 2H), 7.11 (m, 4H), 7.36 (s, 1H). LCMS: m/z for C20H29N6O2P++H observed 417.3 at 1.76 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Aufarbeitung

  1. waitThe mixture was left
  2. customsolvent was evaporated by rotary evaporation
  3. extractionthe product extracted with DCM (3×50 mL)
  4. washCombined organic layers were washed with water (1×50 mL) and brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customProduct was purified by flash column
  7. washeluting 0-20% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b0045bde014a47aa81e4f707cf434555
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338593B2

Notizen zur Reaktion

Wird geladen…