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

HRID 2227453Notes

Reaction equation

HRID 2227453 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8c172b1e59814385bfa354b5508dd3a1
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

Loading…