Imidazole → HCID 10000618, compound

HRID 490265Notes

Reaction equation

HRID 490265 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20](Br)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 210970583-Benzyl-2-(1-bromo-2-methylpropyl)-7-chloroquinazolin-4(3H)-one

Product 1

HCID 10000618HCID 10000618, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-3-benzyl-2-(1-bromo-2-methyl-propyl)-7-chloro-3H-quinazolin-4-one (a compound of Formula 105, 250 mg, 0.616 mmol) in DMF (3 mL) was added triethylamine (0.130 mL, 0.924 mmol) and imidazole (63.0 mg, 0.924 mmol) followed by tetrabutylammonium iodide (228 mg, 0.616 mmol). The resultant solution was heated to 90° C., stirred for 18 h and allowed to cool to room temperature. The reaction mixture was quenched with water (3 mL) and diluted with ether (10 mL). The aqueous layer was extracted with ether (10 mL) ad the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (1:1 hexanes:ethyl acetate) to provide 38 mg (16%) of the title compound as a yellow solid. MS(ES+) m/e 393.0 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with water (3 mL)
  2. additiondiluted with ether (10 mL)
  3. extractionThe aqueous layer was extracted with ether (10 mL) ad the combined extracts
  4. dry with materialwere dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-ed32b4add5b64d8b8e50b0a685c5a26a
Source dataset
uspto-grants-2009_05
Patent number
US07528137B2

Reaction notes

Loading…