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

HRID 2237035Notes

Reaction equation

HRID 2237035 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C[N:20]([CH:22]=O)C.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])=[CH:30][CH:29]=1)=O>O.CCOC(C)=O>[CH2:10]([C:22]1[N:16]([C:15]2[CH:17]=[CH:18][C:12]([O:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[CH:13][CH:14]=2)[CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])=[CH:30][CH:29]=2)[N:20]=1)[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 35808292-(4-Aminophenoxy)naphthaleneHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Product 1

HCID 59699264[3-(4-{2-butyl-1-[4-(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 4-(naphthalen-2-yloxy)aniline (1.2 eq., 5 mmol) in anhydrous DMF (5 mL) DIEA (3 eq. 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-69aa2c4f57d1413b8c5f31898cf317d4
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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