2-Phenylbutane-1,2-diamine → N-(2-amino-2-phenylbutyl)-3-methoxy-2-phenylquinoline-4-carboxamide

HRID 2227453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2227453
[CH3:1][O:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([OH:15])=O)=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:22]1([C:28]([NH2:33])([CH2:31][CH3:32])[CH2:29][NH2:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O.CCOC(C)=O>[NH2:33][C:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH2:31][CH3:32])[CH2:29][NH:30][C:13]([C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[O:2][CH3:1])=[O:15]

Komponenten

7

Edukt 3

HCID 211492-Phenylbutane-1,2-diamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6243483-Methoxy-2-phenylquinoline-4-carboxylic acid

Produkt 1

HCID 22992322N-(2-amino-2-phenylbutyl)-3-methoxy-2-phenylquinoline-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-2-phenylquinoline-4-carboxylic acid (3.0 g), and the compound of step 2 (3.0 g), BOP (5.7 g) and TEA (2.0 g) in 25 mL of anhydrous DMF is stirred at ambient temperature overnight. The mixture is diluted with water and EtOAc. The organic layer is separated, washed with water and concentrated under vacuum. The residue is purified on a silica gel column, eluting with EtOAc and Hexane (1:1) to afford the title compound as white foam.

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with water
  3. concentrationconcentrated under vacuum
  4. customThe residue is purified on a silica gel column
  5. washeluting with EtOAc and Hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c172b1e59814385bfa354b5508dd3a1
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06413982B1

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