Acetic Acid → 6-amino-5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-3-pyridinecarboxamide

HRID 1796521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796521
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])[CH:17]=[N:18][C:19]=2[NH:20]CC=C)=[O:12])=[CH:6][CH:5]=1)[CH3:2].C(O)(=O)C.C1([SiH3])C=CC=CC=1>ClCCl.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>[NH2:20][C:19]1[N:18]=[CH:17][C:16]([C:24]([N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[O:25])=[CH:15][C:14]=1[NH:13][C:11](=[O:12])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 12752PhenylsilaneHCID 221813495-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide

Produkt 1

HCID 221813586-amino-5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-3-pyridinecarboxamideAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a degassed solution of 5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide (1.04 g, 2.53 mmol) in dichloromethane (20 mL) at room temperature was added palladium tetrakis (117 mg, 0.10 mmol), followed by acetic acid (580 μL, 10.14 mmol) and phenyl silane (625 μL, 5.07 mmol). The mixture was stirred for 6 hours. The reaction was then quenched with NaHCO3 saturated aqueous solution (50 mL) and extracted with EtOAc (20 mL). The aqueous phase was back-extracted with additional dichloromethane (2×20 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([3% MeOH+1% NH4OHaq] in CH2Cl2) to provide 705 mg of the title compound 6-amino-5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-3-pyridinecarboxamide (75.2% yield from 5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide). 1H-NMR (400 MHz, CDCl3): δ 1.18 (br s, 6H), 1.43 (t, J=7.0 Hz, 3H), 3.42 (br s, 4H), 3.69 (s, 2H), 4.04 (q, J=7.0 Hz, 2H), 4.73 (s, 2H), 6.91 (d, J=8.6 Hz, 2H), 7.26 (d, J=8.6 Hz, 2H), 7.38 (m, 1H), 7.78 (s, 1H), 7.95 (m, 1H). MS (ESI) (M+H)+: 372.

Aufarbeitung

  1. customThe reaction was then quenched with NaHCO3 saturated aqueous solution (50 mL)
  2. extractionextracted with EtOAc (20 mL)
  3. extractionThe aqueous phase was back-extracted with additional dichloromethane (2×20 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-2e2cdd224680482880a175e7c64d468f
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030139B2

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