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Hydrazinecarboxylic acid, ethyl ester → Tert-butyl(1-(4-(3-oxo-9-phenyl-2,3,5,6-tetrahydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate

HRID 1509112
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1509112
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=S)[NH:23][CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:36](OCC)(=[O:39])[NH:37][NH2:38]>C1COCC1.C([O-])(=O)C.[Hg+]>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24]5=[N:38][NH:37][C:36](=[O:39])[N:23]5[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 123633046Tert-butyl(1-(4-(3-phenyl-5-thioxo-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate

Produkt 1

HCID 123922000Tert-butyl(1-(4-(3-oxo-9-phenyl-2,3,5,6-tetrahydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61181
Mercurous acetate
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl(1-(4-(3-phenyl-5-thioxo-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (55 mg, 0.113 mmol) in THF (7 mL) was added ethyl carbazate (23.6 mg, 0.226 mmol) and mercury acetate (54.1 mg, 0.17 mmol) under nitrogen. The resulting mixture was stirred at r.t. for 2 h. The mixture was concentrated to dryness under reduced pressure and partitioned between DCM (15 ml) and water (15 ml). The organic phase was separated and concentrated to dryness under reduced pressure. The resulting residue was suspended in toluene (7 ml). The resulting mixture was heated under reflux for 3 h. After cooled down to room temperature, the mixture was concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 4% MeOH in dichloromethane) to give tert-butyl(1-(4-(3-oxo-9-phenyl-2,3,5,6-tetrahydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate (32 mg, 56%). LCMS (Method A): RT=6.29 min, M+1=510. 1H NMR (500 MHz, CDCl3): 9.83 (1H,S), 8.10 (1H, s), 7.29 (2H, d), 7.22 (2H, d), 7.19-7.18 (3H, m), 7.13-7.11 (2H, m), 5.1 (1H, br), 4.01 (2H, t), 3.36 (2H, t), 2.43-2.28 (4H, m), 2.02-1.97 (1H, m), 1.76-1.70 (1H, m), 1.30-1.14 (9H, br).

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. custompartitioned between DCM (15 ml) and water (15 ml)
  3. customThe organic phase was separated
  4. concentrationconcentrated to dryness under reduced pressure
  5. temperatureThe resulting mixture was heated
  6. temperatureunder reflux for 3 h
  7. temperatureAfter cooled down to room temperature
  8. concentrationthe mixture was concentrated to dryness under reduced pressure
  9. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 4% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-92b978addba048c4b68aa951eeeaffe2
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221838B2

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