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Potassium Phosphate, Tribasic → 2-{(2-Methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid

HRID 1944573
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944573
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:18][O:19][CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC(N(C)C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:18][O:19][CH2:20][CH2:21][N:22]([CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH3:27])[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)[C:5]([OH:7])=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 167483252-Chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acidHCID 86616985trans (2-Methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride

Produkt 1

HCID 694982882-{(2-Methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851
HCID 178418851, Verbindung
Katalysator
HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A suspension of 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acid (20 g, 75.6 mmol), trans (2-methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride (17.65 g, 98.2 mmol), potassium phosphate (48.12 g, 226.7 mmol) in DMA (300 mL) was degassed with argon for 10 min. Pd(PtBu3)2 (1.93 g, 3.78 mmol) was added and the reaction mixture was degassed with argon for 10 min. The reaction mixture was stirred at 110° C. for 24 hours. The reaction was cooled to rt, filtered through celite, rinsed with EtOAc, diluted with water, the pH was adjusted to 3-4 with 1N HCl, extracted with EtOAc (×3). The organic layer was washed with aq LiCl, dried over sodium sulfate and concentrated in vacuo to give 2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid. 1H NMR (400 MHz, CDCl3) δ 7.05 (s, 1H), 7.62 (s, 1H), 3.76 (t, J=6.3 Hz, 2H), 3.60 (t, J=6.3 Hz, 2H), 3.52-3.43 (m, 1H), 3.39 (s, 3H), 3.36 (s, 3H), 3.38-3.30 (m, 1H), 3.18 (s, 3H), 1.23 (d, J=6.1 Hz, 3H), 0.82-0.64 (m, 2H), 0.46-0.39 (m, 1H), 0.32-0.25 (m, 1H).

Aufarbeitung

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture was degassed with argon for 10 min
  3. temperatureThe reaction was cooled to rt
  4. filtrationfiltered through celite
  5. washrinsed with EtOAc
  6. additiondiluted with water
  7. extractionextracted with EtOAc (×3)
  8. washThe organic layer was washed with aq LiCl
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0451064183eb489cbd137ccbe32d1122
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394837B2

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