Water → HCID 70154558, compound

HRID 2187078Notes

Reaction equation

HRID 2187078 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:10](=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:22])[CH:8]=2)[N:3]1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].[CH2:53](Br)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.O>CN(C)C=O>[CH2:53]([O:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH:34]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:29][CH2:28]1)[C:2](=[O:1])[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:10]2=[O:21])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 17795944HCID 17795944, compound

Product 1

HCID 70154558HCID 70154558, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl 2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-6-hydroxy-1,2,3,4-tetrahydroquinazoline-3-valerate (1.34 g, 2.13 mmol) obtained in Example 105 and potassium carbonate (354 mg, 2.56 mmol) in N,N-dimethylformamide (50.0 ml), benzyl bromide (305 ml, 2.56 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 18.5 hours. The reaction mixture was combined with water and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4) the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluting with n-hexane-ethyl acetate (5:1, v/v) to give the ethyl ester of the title compound (450 mg, 29%) as an oil.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. washAfter the extract was washed with water
  4. dry with materialdried (MgSO4) the solvent
  5. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-fbb4fc79b57b48ccac88d2507de596f4
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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