Dimethylformamide → N-(3-cyanophenyl)-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-4-biphenylcarboxamide

HRID 131670

Reaktionsgleichung

Reaktionsgleichung von HRID 131670
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1.C(Cl)(=O)C(Cl)=O.[C:29]([C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34])#[N:30].CN(C=O)C>CN(C=O)C.C(Cl)Cl>[C:29]([C:31]1[CH:32]=[C:33]([NH:34][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:3]3[CH:4]=[C:5]([C:8]4[O:9][C:10]([CH3:13])=[N:11][N:12]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:19][CH:18]=2)=[O:22])[CH:35]=[CH:36][CH:37]=1)#[N:30]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 167023-AminobenzonitrileHCID 65578Oxalyl chlorideHCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

Produkt 1

HCID 10200651N-(3-cyanophenyl)-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-4-biphenylcarboxamideAusbeute 8,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2′-Methyl-5′-(5methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (100 mg, 0.34 mmol), oxalyl chloride (0.03 ml, 0.41 mmol), and DMF (1 drop) were mixed in DCM (5 ml) and stirred at room temperature for 35 min. 3-Cyanoaniline (44 mg, 0.374 mmol) was added to the solution and the mixture stirred for 2 h; DMF (1 ml) was added and stirring continued for 18 h. The solvents were evaporated from the reaction under vacuum and the residue chromatographed on an SPE (silica, 5 g), eluting with DCM and then DCM/ethanol/ammonia (300:8:1). The product fractions were concentrated in vacuo to give N-(3-cyanophenyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide as a white solid (11 mg, 8%). NMR; δH [2H6]—DMSO 10.65,(1H, b), 8.28,(1H, m), 8.07,(3H, m), 7.91,(1H, dd), 7.79,(1H, d), 7.62-7.56,(5H, m), 2.57,(3H, s), 2.33,(3H, s). LCMS; retention time 3.49 min, MH+ 395

Aufarbeitung

  1. stirringthe mixture stirred for 2 h
  2. stirringstirring
  3. waitcontinued for 18 h
  4. customThe solvents were evaporated from the reaction under vacuum
  5. customthe residue chromatographed on an SPE (silica, 5 g)
  6. washeluting with DCM
  7. concentrationThe product fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72b868ef9d9a41c38ebbbc5dedcfa2cf
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384963B2

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