Sodium Hydroxide → 3-Bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylic acid

HRID 2208806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208806
[Br:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[N:8]([CH3:15])[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[N:8]([CH3:15])[CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86719561Methyl 3-bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylate

Produkt 1

HCID 867195623-Bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylic acidAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 3-bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylate (102 mg, 0.28 mmol) in THF (2 ml) was added 2M aqueous NaOH (0.70 ml, 1.40 mmol) and the reaction mixture was left to stir at room temperature for 18 h after which time the THF was evaporated in vacuo. The aqueous phase was then treated with an aqueous 10% citric acid solution to 5-6 and then extracted with EtOAc (3×50 ml) followed by a solution of 1:1 IPA/CHCl3 (2×50 ml), the combined organic phases were then washed with brine (50 ml) dried with Na2SO4 and evaporated to give the title compound as a white solid (72 mg, 73%). LC-MS 100%, 1.49 min (3.5 minute LC-MS method), m/z=349.0/351.0/352.9, 1H NMR (500 MHz, Methanol-d4) δ 7.07 (s, 1H), 4.02 (dd, J=11.3, 4.3 Hz, 2H), 3.96-3.87 (m, 1H), 3.46 (t, J=11.0 Hz, 2H), 2.85 (s, 3H), 1.96 (dd, J=12.3, 4.3 Hz, 2H), 1.77 (s, 2H).

Aufarbeitung

  1. waitthe reaction mixture was left
  2. customwas evaporated in vacuo
  3. additionThe aqueous phase was then treated with an aqueous 10% citric acid solution to 5-6
  4. extractionextracted with EtOAc (3×50 ml)
  5. washthe combined organic phases were then washed with brine (50 ml)
  6. dry with materialdried with Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8c3f9a38355342198295bae36a72e689
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376422B2

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