Ethyl Acetate → 2-(5-Amino-2-bromophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1198695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1198695
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:20][C:19]=2[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[CH:20][C:19]=3[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]2)[CH:4]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 103494052-(2-Bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Produkt 1

HCID 191027882-(5-Amino-2-bromophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-oneAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred solution of 200 mg (0.303 mmol) of 2-(2-bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C) in 3.5 mL of THF was cooled to 0° C. and treated dropwise with a solution of 542 mg (2.4 mmol) of stannous chloride dihydrate in 1.5 mL of concentrated hydrochloric acid. After 45 minutes, the mixture was added to a vigorously stirred mixture of 50% NaOH and ice. Ethyl acetate (15 mL) was added, and the mixture was stirred at 0° C. for 1.5 hours. The phases were separated, and the aqueous fraction was re-extracted twice with ethyl acetate. The combined organic fractions were washed with water and brine and dried over anhydrous Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed on silica gel to give 131 mg (68%) of the title compound as a stiff, off-white foam, mp 103°-105° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 629, 631 (M+1)+.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous fraction was re-extracted twice with ethyl acetate
  3. washThe combined organic fractions were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe filtered solution was concentrated
  6. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-edb8436370164420b48b4f6103cc0c8f
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281614

Notizen zur Reaktion

Wird geladen…