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Triethylamine → HCID 178423845, Verbindung

HRID 1867174
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1867174
[Br:1][C:2]1[C:3](=[O:34])[N:4]([C:19]2[CH:20]=[C:21]([C:26](=O)[CH2:27][C:28]([O:30]CC)=[O:29])[CH:22]=[CH:23][C:24]=2[CH3:25])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].C([N:37](CC)CC)C.Cl.NO.C([O-])(O)=O.[Na+]>CCO.C(Cl)Cl.[Cl-].[Na+].O>[Br:1][C:2]1[C:3](=[O:34])[N:4]([C:19]2[CH:20]=[C:21]([C:26]3[CH:27]=[C:28]([OH:30])[O:29][N:37]=3)[CH:22]=[CH:23][C:24]=2[CH3:25])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471Triethylamine3×HCID 443297Hydroxyamine hydrochloride3×HCID 516892Sodium BicarbonateHCID 22050332ethyl 3-{3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylphenyl}-3-oxopropanoate

Produkt 1

HCID 178423845HCID 178423845, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-{3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylphenyl}-3-oxopropanoate (0.20 g, 0.37 mmol), triethylamine (0.06 mL, 0.41 mmol), and hydroxylamine hydrochloride (0.03 g, 0.41 mmol) in EtOH (3.00 mL) was heated overnight at 60° C. with a condenser. Additional triethylamine (0.06 mL) and hydroxylamine hydrochloride (0.03 g) were added. After 2.5 h, the additions of triethylamine and hydroxylamine hydrochloride were repeated. After 1 h, the reaction was concentrated and purified by preparatory HPLC. The product was isolated by freeze-drying and evaporation of the solvent to give a white solid. Dissolved solid in DCM. Upon addition of 5% NaHCO3, solution became a milky emulsion. Added additional DCM and some brine. Organic extracts were dried over Na2SO4, filtered, and concentrated to a pink solid, dried in vacuo (120 mg, 64%). 1H NMR (CD3OD/400 MHz) δ 7.66 (m, 2H), 7.44 (m, 2H), 7.04 (t, 2H, J=8.8 Hz), 6.64 (s, 1H), 5.36 (s, 2H), 2.04 (s, 3H), 2.01 (s, 3H). ESHRMS m/z 503.0415 and 505.0402 (M+H calculated for C23H18BrF2N2O4 requires 503.0413 and 505.0395).

Aufarbeitung

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated
  3. custompurified by preparatory HPLC
  4. customThe product was isolated
  5. customby freeze-drying
  6. customevaporation of the solvent
  7. customto give a white solid
  8. dry with materialOrganic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to a pink solid
  11. customdried in vacuo (120 mg, 64%)

Quellen und Nachweise

ORD-Eintrag
ord-4ecb85449bc14787b20b43f19b4634c7
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07629363B2

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