Hydrochloric Acid → HCID 86752617, compound

HRID 1292077Notes

Reaction equation

HRID 1292077 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 MgSO4, 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. Analysis calculated for C25H22 N4O5 : C, 65.49; H, 4.84; N, 12.22. Found: C, 65.49; H, 4.84; N, 12.03.

Workup

  1. concentrationconcentrated
  2. additionIt was then diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-8617cdabbb9840a4b623fffb680e63fb
Source dataset
uspto-grants-1998_05
Patent number
US05756502

Reaction notes

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