3-Aminobenzonitrile → N-(3-cyanophenyl)-4-methyl-1,2,5-oxadiazole-3-carboxamide

HRID 1845752

Reaktionsgleichung

Reaktionsgleichung von HRID 1845752
[CH3:1][C:2]1[C:3]([C:7]([OH:9])=O)=[N:4][O:5][N:6]=1.[NH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:14]([C:13]1[CH:12]=[C:11]([NH:10][C:7]([C:3]2[C:2]([CH3:1])=[N:6][O:5][N:4]=2)=[O:9])[CH:18]=[CH:17][CH:16]=1)#[N:15]

Komponenten

6

Edukt 3

HCID 167023-AminobenzonitrileHCID 81531DiisopropylethylamineHCID 3147684-Methyl-1,2,5-oxadiazole-3-carboxylic acid

Produkt 1

HCID 58941863N-(3-cyanophenyl)-4-methyl-1,2,5-oxadiazole-3-carboxamideAusbeute 6,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

4-Methyl-1,2,5-oxadiazole-3-carboxylic acid (200 mg, 1.6 mmol) and bromotris-(pyrrolydino)phosphonium hexafluorophosphate was dissolved in a 1/1 mixture of DMF/DCM. To the mixture was added DMAP (120 mg, 0.95 mmol) and 3-amino-benzonitrile (184 mg, 1.6 mol) followed by N,N-diisopropylethylamine. The reaction mixture was stirred at rt overnight. The volatiles were removed in vacuo and the residue dissolved with chloroform and loaded onto a 40 g Silica ISCO cartridge eluting with 25%-50% EtOAc/Hexane to afford a white powder (25 mg). MF=C11H8N4O2; LCMS calculated for C11H9N4O2(M+H)+: m/z=229.1.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved with chloroform
  3. washeluting with 25%-50% EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-80e4a47c190c4dc1952c2be51ca35483
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08951536B2

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