Dimethylformamide → [3-(4-{2-butyl-1-[4-(6-methoxy-naphthalen-2-yloxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

HRID 17710Notes

Reaction equation

HRID 17710 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2.C[N:22]([CH:24]=O)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[CH:32][CH:31]=1)=O>O.CCOC(C)=O>[CH2:4]([C:24]1[N:18]([C:17]2[CH:19]=[CH:20][C:14]([O:13][C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=3)=[CH:15][CH:16]=2)[CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[CH:32][CH:31]=2)[N:22]=1)[CH2:3][CH2:12][CH3:11]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 669775184-(6-Methoxy-naphthalen-2-yloxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Product 1

HCID 59699185[3-(4-{2-butyl-1-[4-(6-methoxy-naphthalen-2-yloxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of an 4-(6-methoxy-naphthalen-2-yloxy)aniline (5 mmol) in anhydrous DMF (20 mL) DIEA (15 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (4.6 mmol), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC or HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was used for further transformation without additional purification.

Workup

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

Sources & evidence

ORD record
ord-33f73c6c496f494dbfd9000b3a825d57
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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