Butyl bromide → HCID 70434657, compound

HRID 2308695Notes

Reaction equation

HRID 2308695 reaction equation
[CH:1]1([N:7]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8](=[O:27])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]2[NH:23][C:24](=[O:26])[CH2:25][N:17]2[CH2:16]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:36][CH2:37][CH2:38][CH3:39]>CN(C)C=O>[CH:1]1([N:7]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8](=[O:27])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]2[N:23]([CH2:36][CH2:37][CH2:38][CH3:39])[C:24](=[O:26])[CH2:25][N:17]2[CH2:16]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 136142467HCID 136142467, compound

Product 1

HCID 70434657HCID 70434657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(N-cyclohexyl-4-(2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutyramidyl)acetate in dry dimethylformamide was added sodium hydride (1.05 equivalents). The mixture was stirred at 60° C. for 30 minutes to give a homogeneous solution. 1-Bromobutane (1.1 equivalents) was added via a syringe after which the mixture was evaporated. The residue was dissolved in ethyl acetate and washed with saturated brine, dried and filtered. Evaporation of the solvent afforded methyl 2-(N-cyclohexyl-4-(1-butyl-2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutyramidyl)acetate.

Workup

  1. customto give a homogeneous solution
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated brine
  5. customdried
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9dcdb24d0a6c44439676881ab3f516b1
Source dataset
uspto-grants-1987_09
Patent number
US04690925

Reaction notes

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