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1-Phenethylamine, (-)- → 5-(1-(t-butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897406
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 897406
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35](Cl)[CH:34]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:40][C@H:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:48][C@H:41]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH3:40])[CH:34]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 758181-Phenethylamine, (-)-HCID 634876Binap, (A+-)-HCID 223465805-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 20816904
5-(1-(t-butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (0.93 g, 1.7 mmol), (S)-α-methylbenzylamine (0.48 g, 4 mmol), palladium acetate (0.06 g, 0.26 mmol) and racemic BINAP (0.16 g, 0.26 mmol) were combined in toluene (15 ml) and the resulting solution was degassed with nitrogen. Sodium t-butoxide (0.48 g, 5 mmol) was added and the resulting mixture was heated to 90° C. for 1 hour. The mixture was partitioned between sat. ammonium chloride and ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to a syrup. The residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane) gave the product as a syrup; MS m/z (M+H)+ 642.4; C35H34F3N7O2 require 641.3.

Aufarbeitung

  1. customthe resulting solution was degassed with nitrogen
  2. customThe mixture was partitioned between sat. ammonium chloride and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a syrup
  7. customThe residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1d79ef9174754f0fa6cf6c9d5a4a4f45
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06921762B2

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