4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 917696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917696
[F:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([OH:15])=O)=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.[NH2:21][O:22][CH2:23][CH2:24][OH:25].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CO.C1COCC1>[F:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:21][O:22][CH2:23][CH2:24][OH:25])=[O:15])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Komponenten

5

Edukt 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 3014186Ethanol, 2-(aminooxy)-HCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Produkt 1

HCID 112130144-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (130 mg, 0.34 mmol) and 2-(aminooxy)ethanol [prepared by the literature procedure: Dhanak, D.; Reese, C. B., J. Chem. Soc., Perkin Trans. 1, 1987; 2829] (52 mg, 0.67 mmol) in MeOH/THF (1:1, 20 mL) was added DMT-MM (187 mg, 0.67 mmol) and the mixture stirred at R.T. for 15 h. The reaction solvent was removed under reduced pressure and the oily residue partitioned between water (100 mL) and EtOAc (100 mL). The EtOAc fraction was then washed with water (2×100 mL) and brine (100 mL), dried (Na2SO4) and the solvent removed under reduced pressure. This afforded a cream solid which was purified by recrystallisation from EtOAc/MeOH to give 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white, crystalline solid (83 mg, 55%), m.p. (EtOAc/MeOH) 148-151° C. 1H NMR [(CD3)2SO, 400 MHz] δ 11.65 (v br s, 1H), 9.48 (br s, 1H), 8.13 (s, 1H), 7.74 (dd, J=10.2, 1.8 Hz, 1H), 7.58 (br d, J=8.6 Hz, 1H), 7.28 (t, J=8.5 Hz, 1H), 5.55 (s, 1H), 4.76 (v br s, 1H), 3.90 (t, J=4.9 Hz, 2H), 3.61 (t, J=4.9 Hz, 2H), 3.36 (s, 3H). Anal. Calcd for C15H15FIN3O4: C, 40.3; H, 3.4; N, 9.4. Found: C, 40.6; H, 3.6; N, 9.1.

Aufarbeitung

  1. customprepared by the literature procedure
  2. customThe reaction solvent was removed under reduced pressure
  3. customthe oily residue partitioned between water (100 mL) and EtOAc (100 mL)
  4. washThe EtOAc fraction was then washed with water (2×100 mL) and brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. customThis afforded a cream solid which
  8. customwas purified by recrystallisation from EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-8fe8c8f6b5d444d3af8f16bb70f02452
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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