Trifluoroacetic acid → HCID 67249920, Verbindung

HRID 524115

Reaktionsgleichung

Reaktionsgleichung von HRID 524115
Br[C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[N:8][N:7]=[C:6]1[N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19]C(=O)OC(C)(C)C)[CH2:14]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][N:13]([C:6]2[N:5]([CH2:4][C:3]3[CH:2]=[CH:30][CH:29]=[C:28]([F:31])[CH:27]=3)[C:10](=[O:11])[C:9]([CH3:12])=[N:8][N:7]=2)[CH2:14]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58328539(R)-tert-butyl 1-(4-(2-bromo-5-fluorobenzyl)-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)piperidin-3-ylcarbamate

Produkt 1

HCID 67249920HCID 67249920, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl 1-(4-(2-bromo-5-fluorobenzyl)-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)piperidin-3-ylcarbamate (18, 30 mg) in dichloromethane (1 mL) was added TFA (0.5 mL), and the mixture was stirred at RT for 3 h. The mixture was carefully neutralized with NaHCO3 (aq, saturated), and extracted with CH2Cl2 (10 mL×3). The combined extracts were dried over Na2SO4 and concentrated to give the crude product. This was purified by column chromatography on silica gel, and eluted with 92:6:2 dichloromethane-methanol-ammonia to provide (R)-3-(3-aminopiperidin-1-yl)-4-(3-fluorobenzyl)-6-methyl-1,2,4-triazin-5(4H)-one (19). MS: m/z, 396 (100%, M+1), 398 (100%).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (10 mL×3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product
  5. customThis was purified by column chromatography on silica gel
  6. washeluted with 92:6:2 dichloromethane-methanol-ammonia

Quellen und Nachweise

ORD-Eintrag
ord-706dbfc53505421a8c2a61e27d6edd5c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340523B2

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