Triphenylphosphine dibromide → Tert-butyl 4-(5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)benzylcarbamate

HRID 2204866

Reaktionsgleichung

Reaktionsgleichung von HRID 2204866
[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH:23][C:24]([C:26]2[CH:40]=[CH:39][C:29]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:27]=2)=[O:25])=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[NH2:1][C:2]1[C:3]([C:20]2[O:25][C:24]([C:26]3[CH:27]=[CH:28][C:29]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:39][CH:40]=3)=[N:23][N:22]=2)=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 59471855Tert-butyl 4-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinecarbonyl)benzylcarbamate

Produkt 1

HCID 59471911Tert-butyl 4-(5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)benzylcarbamateAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinecarbonyl)benzylcarbamate (136 mg, 0.24 mmol) and DIPEA (109.8 mg, 148.0 μL, 0.8499 mmol) in acetonitrile (3.000 mL) at 0° C. was treated portionwise with dibromo(triphenyl)phosphorane (143.5 mg, 0.3400 mmol) and the resulting mixture stirred at room temperature for 48 h. The mixture was concentrated in vacuo and pre-absorbed onto silica gel and purified by column chromatography on silica gel eluting with 50% EtOAc/CH2Cl2 to give the product (46.8 mg, 30% yield); MS (ES+) 551.31

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompre-absorbed onto silica gel
  3. custompurified by column chromatography on silica gel eluting with 50% EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e76e1275522b4e54acfabe3f60724dbf
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365557B2

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