1-(4-Bromobenzene-1-sulfonyl)piperazine → 2-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-propyl-3H-quinazolin-4-one

HRID 238198Notes

Reaction equation

HRID 238198 reaction equation
Br[CH:2]([C:4]1[N:13]([CH2:14][CH2:15][CH3:16])[C:12](=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(O)C>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]2[CH2:33][CH2:32][N:31]([CH:2]([C:4]3[N:13]([CH2:14][CH2:15][CH3:16])[C:12](=[O:17])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH3:3])[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7129241-(4-Bromobenzene-1-sulfonyl)piperazineHCID 599931882-(1-bromo-ethyl)-3-propyl-3H-quinazolin-4-one

Product 1

HCID 119578302-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-propyl-3H-quinazolin-4-oneYield 13.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(1-bromo-ethyl)-3-propyl-3H-quinazolin-4-one (30 mg, 0.1 mmol) and 1-(4-bromo-benzenesulfonyl)-piperazine (47 mg, 0.15 mmol) in ethanol (1 mL) was refluxed overnight. The reaction mixture was then concentrated in vacuo and purified by reverse phase HPLC to yield the product as a white powder (7 mg, 9%). 1H NMR (CDCl3) δ 1.03 (t, 3H, J=5.8 Hz), 1.72 (sex, 2H, J=6.0), 1.80 (d, 3H, J=5.2), 3.48 (m, 6H), 3.90 (m, 3H), 4.23 (m, 1H), 4.77 (q, 1H, J=5.2 Hz), 7.58 (m, 3H), 7.68 (d, 1H, J=6.5 Hz), 7.72 (d, 2H, J=7.1 Hz), 7.81 (t, 1H, J=6.2 Hz), 8.28 (d, 1H, J=6.5 Hz).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-74b88ef3f0bb430fb936832d66b3de64
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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