2-Phenylpropylamine → 2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-phenylpropyl)-1,1'-biphenyl-4-carboxamide

HRID 131748

Reaktionsgleichung

Reaktionsgleichung von HRID 131748
[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](O)=[O:21])=[CH:16][CH:15]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[C:45]1([CH:51]([CH3:54])[CH2:52][NH2:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C>[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]([NH:53][CH2:52][CH:51]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH3:54])=[O:21])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 113982-PhenylpropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

Produkt 1

HCID 102730492'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-phenylpropyl)-1,1'-biphenyl-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (11.3 mg, 0.034 mmol), HOBT (6.0 mg, 0.044 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (8.0 mg, 0.042 mmol) and 2-phenylpropylamine (0.34 mmol) were mixed in DMF (0.7 ml) and the reaction left at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (0.4 ml) and water (0.4 ml). The organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml) and the DCM evaporated under vacuum. The residue was purified by mass directed HPLC to give 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-phenylpropyl)-1,1′-biphenyl-4-carboxamide. LCMS; retention time 3.44 min, MH+ 412.

Aufarbeitung

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (0.4 ml) and water (0.4 ml)
  3. washThe organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml)
  4. customthe DCM evaporated under vacuum
  5. customThe residue was purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-fe8f967f3eb04dc68cc4ac89da599f95
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384963B2

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