Triethylamine → (+/-)-4-bromo-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]benzamide

HRID 1827265Notes

Reaction equation

HRID 1827265 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]=[C:10]([NH:33]C(C3OC=CC=3)=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([OH:48])=O)=[CH:44][CH:43]=1.Cl.C(C(NCCCN(C)C)=N)C.ON1C2C=CC=CC=2N=N1.CCN(CC)CC>C1COCC1.O.CCOC(C)=O>[Br:41][C:42]1[CH:43]=[CH:44][C:45]([C:46]([NH:33][C:10]2[CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]=2)=[O:48])=[CH:49][CH:50]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 114644-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 22136488(+/-)-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]-2-furancarboxamideHCID 178458058HCID 178458058, compound

Product 1

HCID 22136480(+/-)-4-bromo-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]benzamideYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (±)-2-amino-4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-6-quinolinemethanol (0.000210 mol) (see Example B8), 4-bromo-benzoic acid (0.000252 mol), N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine monohydrochloride (0.000315 mol), 1-hydroxy-1H-benzotriazole (0.000315 mol; 1.5 equiv) and Et3N (0.000315 mol) in THF (2 ml) was stirred for 18 hours at room temperature, then taken up into EtOAc and H2O. The organic layer was separated and the solvent evaporated. The residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding 0.065 g (41%) of (±)-4-bromo-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]benzamide, MS (ESI) m/z: 657 659 661 663.

Workup

  1. customThe organic layer was separated
  2. customthe solvent evaporated
  3. customThe residue was purified by HPLC
  4. customThe product fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cef8c02e99144ebfb303a8e4979fd3ae
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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