Hydrochloric Acid → HCID 86752617, compound

HRID 362604Notes

Reaction equation

HRID 362604 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([NH:14][C:15]2[N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH:32]([CH3:34])[CH3:33])[CH:26]=3)[C:23](=[O:35])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[O:13])[CH:6]=1)C.[Li+].[OH-].Cl>O1CCOCC1>[CH:32]([O:31][C:27]1[CH:26]=[C:25]([N:24]2[C:23](=[O:35])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]2[NH:14][C:12](=[O:13])[NH:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:36])=[O:3])[CH:30]=[CH:29][CH:28]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86752618HCID 86752618, compound

Product 1

HCID 86752617HCID 86752617, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-{3-[3-(3-Isopropoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-ureido}-benzoic acid ethyl ester (200 mg, 0.41 mmol) in 1,4-dioxane (10 mL) was added 1N LiOH (3 mL) and stirred overnight. The reaction mixture was acidified with 1N HCl and concentrated. It was then diluted with ethyl acetate and washed with water. The organic layer was dried over MgSO41 concentrated and chromatographed using ethyl acetate:hexane (1:1 v/v) to isolate pure product as a white solid (150 mg, 80.2%), mp 158°-160° C.

Workup

  1. concentrationconcentrated
  2. additionIt was then diluted with ethyl acetate
  3. washwashed with water
  4. customThe organic layer was dried over MgSO41
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-9e11f40e359149a08ea2786c5eeb615f
Source dataset
uspto-grants-1999_02
Patent number
US05869665

Reaction notes

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