N-bromobutanimide → {1-[4-(3-Bromo-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362157Notes

Reaction equation

HRID 2362157 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[CH:30]=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:41])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[C:30]([Br:41])=[CH:31][N:32]=[C:20]4[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66668862{1-[4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

Product 1

HCID 66665726{1-[4-(3-Bromo-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterYield 127.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 4-1 (100 mg, 0.227 mmol) in CHCl3 (5 mL) was added NBS (40 mg 0.227 mmol.) and the mixture was heated to reflux for 2 hrs. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HCl(aq) and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 150 mg of 4-3.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. temperatureAfter cooling
  4. washthe combined organic phase was washed with 0.1N HCl(aq) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-844c4b00b90a4ffe82d860da813a8fab
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

Loading…