Acetic Anhydride → 1-(4-{2-[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-ethyl}-piperazin-1-yl)-ethanone

HRID 2101498Notes

Reaction equation

HRID 2101498 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[CH3:33][C:34](OC(C)=O)=[O:35].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([C:34](=[O:35])[CH3:33])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 11949835[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-(2-piperazin-1-yl-ethyl)-amine

Product 1

HCID 119553611-(4-{2-[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-ethyl}-piperazin-1-yl)-ethanoneYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-(2-piperazin-1-yl-ethyl)-amine (55 mg, 0.12 mmol) in CH2Cl2 at ambient temperature was added dropwise Ac2O (34 μL, 0.36 mmol). The mixture was stirred for 2 h before addition of saturated NaHCO3 (6 mL). The mixture was extracted with CH2Cl2 (2×20 mL) and the combined extracts dried over Na2SO4 then concentrated in vacuo. The residue was purified by semi-preparative HPLC to provide the title compound (42 mg, 66%) as a viscous oil: ESI MS m/z 518 [C26H30Cl2FN5O+H]+.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (2×20 mL)
  2. dry with materialthe combined extracts dried over Na2SO4
  3. concentrationthen concentrated in vacuo
  4. customThe residue was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-46bb9d3f48d04e7e9d6e93655f56ceca
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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