Methyl iodide → HCID 57442342, compound

HRID 2262719Notes

Reaction equation

HRID 2262719 reaction equation
N1([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[O:7])C=CN=C1.CI.[CH:25]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1>C(#N)C.C(Cl)Cl>[CH:25]1([N:29]2[CH2:34][CH2:33][N:32]([C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]4[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=4)[CH2:10][CH2:9]3)=[O:7])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 47386021-CyclobutylpiperazineHCID 4784736HCID 4784736, compound

Product 1

HCID 57442342HCID 57442342, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{4-[4-(imidazole-1-carbonyl)-piperazin-1-yl]-phenyl}-ethanone (8 mmol) in acetonitrile (15 mL) is added MeI (32 mmol). The mixture is stirred at rt for 24 h. Solvent is removed in vacuo to yield a light yellow solid. The solid is dissolved in DCM (40 mL), followed by the addition of 1-cyclobutylpiperazine (8 mmol) and TEA (8 mmol). The mixture is stirred at rt for 24 h, washed with aqueous sodium bicarbonate (20 mL). The organic layer is dried over MgSO4 and solvent removed to give the crude product, which is purified by column chromatography (5% MeOH in DCM) to give the pure title compound. 1H NMR (300 MHz, CDCl3) δ 7.87 (d, 2H), 6.86 (d, 2H), 3.49-3.33 (m, 12H), 2.76-2.71 (m, 1H), 2.53 (s, 3H), 2.32 (t, 4H), 2.05-2.01 (m, 2H), 1.91-1.85 (m, 2H), 1.76-1.69 (m, 2H); LC-MS (M+1) 371.1.

Workup

  1. customSolvent is removed in vacuo
  2. customto yield a light yellow solid
  3. stirringThe mixture is stirred at rt for 24 h
  4. washwashed with aqueous sodium bicarbonate (20 mL)
  5. dry with materialThe organic layer is dried over MgSO4 and solvent
  6. customremoved
  7. customto give the crude product, which
  8. customis purified by column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-66967cc5332c444c96ee1dc1e587aa97
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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