Bis(2-bromoethyl) ether → 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-[2-methyl-5-(2-morpholin-4-yl-ethyl)-imidazol-1-ylmethyl]-benzonitrile

HRID 1594863Notes

Reaction equation

HRID 1594863 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4([CH2:36][CH3:37])[CH2:33][CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[C:28]4=[O:35])[CH:22]=3)[CH:13]=2)[C:9]([CH3:38])=[N:8][CH:7]=1.Br[CH2:40][CH2:41][O:42][CH2:43][CH2:44]Br>C(#N)C.C(N(CC)CC)C>[CH2:36]([C:27]1([C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[O:20][C:14]2[CH:13]=[C:12]([CH2:11][N:10]3[C:6]([CH2:5][CH2:4][N:3]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:7][N:8]=[C:9]3[CH3:38])[CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:33][CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[C:28]1=[O:35])[CH3:37]

Participants

5

Reactant 2

HCID 21521Bis(2-bromoethyl) etherHCID 217062014-[5-(2-Amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride

Product 1

HCID 98077692-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-[2-methyl-5-(2-morpholin-4-yl-ethyl)-imidazol-1-ylmethyl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[5-(2-amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride (as described in Example 11) (0.25 g, 0.456 mmol) in acetonitrile (35.0 mL) and triethylamine (1.8 mL) was added 2-bromoethyl ether (0.133 mL, 1.06 mmol) and the mixture was refluxed for 48 hr. The solvents were removed in vacuo to obtain the title compound after purification by preparative HPLC.

Workup

  1. temperaturethe mixture was refluxed for 48 hr
  2. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-aa3eb88c8e6c445794e16d41429514f0
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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