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p-Toluenesulfonic acid → (S)-4-Amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-hydroxypicolinamide

HRID 2370874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2370874
[NH2:1][C:2]1[C:7]([O:8]C)=[CH:6][N:5]=[C:4]([C:10]([NH:12][C@@H:13]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[C:23]([F:32])[CH:22]=2)[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:11])[CH:3]=1.[Li+].[Cl-].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.CCOC(C)=O>[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][N:5]=[C:4]([C:10]([NH:12][C@@H:13]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[C:23]([F:32])[CH:22]=2)[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:11])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 71144233(S)-4-Amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxypicolinamide

Produkt 1

HCID 71144326(S)-4-Amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-hydroxypicolinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a stirred solution of (S)-4-amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl) (3-fluoropyridin-2-yl)methyl)-5-methoxypicolinamide (600 mg, 0.0013 mol) in NMP (10 mL) was added LiCl (168 mg, 0.0039 mol, Aldrich) followed by pTSA (754 mg, 0.0039 mol, Aldrich) at rt. The reaction mixture was stirred at 180° C. for 2 h. After completion of the reaction (monitored by TLC, 50% EtOAc in petroleum ether), the reaction mixture was cooled to room temperature and sat'd NaHCO3 (50 mL) was added and the aqueous solution was extracted with EtOAc (25 mL×2). The combined organic layers were washed with water (25 mL×2), saturated NaCl (25 mL) and dried over anhydrous sodium sulfate. The product thus obtained was purified by silica gel (60-120 mesh) column chromatography eluting with 60-70% EtOAc in petroleum ether to give the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.51 (d, J=8 Hz, 1H), 8.55 (d, J=4.8 Hz, 1H), 7.82-7.78 (m, 2H), 7.56-7.50 (m, 2H), 7.46 (d, J=1.6 Hz, 10.4 Hz, 1H), 7.30 (d, J=12.8, 2H), 6.48 (d, J=4.4 Hz, 1H), 5.78 (s, 2H). MS (ESI, positive ion) m/z: 441.3 (M+H).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionthe aqueous solution was extracted with EtOAc (25 mL×2)
  3. washThe combined organic layers were washed with water (25 mL×2), saturated NaCl (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe product thus obtained
  6. customwas purified by silica gel (60-120 mesh) column chromatography
  7. washeluting with 60-70% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-e222ed31f8a14b4b97bd790ba2ccae90
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710043B2

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