Potassium Iodide → 2-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

HRID 238233Notes

Reaction equation

HRID 238233 reaction equation
Br[CH:2]([C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:24]2[CH2:29][CH2:28][N:27]([CH:2]([C:4]3[N:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH3:3])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 7129241-(4-Bromobenzene-1-sulfonyl)piperazineHCID 599931212-(1-Bromo-ethyl)-quinazoline

Product 1

HCID 599933482-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(1-Bromo-ethyl)-quinazoline (43 mg, 0.18 mmol) and 1-(4-Bromo-benzenesulfonyl)-piperazine (67 mg, 0.22 mmol), potassium iodide (30 g, 0.18 mmol) and potassium carbonate (37 mg, 0.27 mmol) in acetonitrile (1 mL) was heated at 65° C. for 1 day. The reaction mixture was then concentrated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium thiosulphate solution, saturated sodium bicarbonate solution and then with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was dissolved in DMSO and purified by HPLC. 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.06 (m, 3H), 7.80 (t, J=7.9 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 4.86 (q, J=7.0 Hz, 1H), 3.65 (m, 2H), 3.43 (m, 6H), 1.88 (d, J=7.0 Hz, 3H) HPLC ret. time 2.45 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 461.1 (M+1)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium thiosulphate solution, saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in DMSO
  7. custompurified by HPLC
  8. custom1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.06 (m, 3H), 7.80 (t, J=7.9 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 4.86 (q, J=7.0 Hz, 1H), 3.65 (m, 2H), 3.43 (m, 6H), 1.88 (d, J=7.0 Hz, 3H) HPLC ret. time 2.45 min, 10-99% CH3CN, 5 min

Sources & evidence

ORD record
ord-87a4c362569442169dae661859783a5f
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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