Hydrochloric Acid → {1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid

HRID 472741Notes

Reaction equation

HRID 472741 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][N:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:15][C:16](=[O:29])[NH:17][C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH3:26])=[CH:20][C:19]=2[O:27][CH3:28])[C:6]1=[O:30].[OH-].[K+].Cl>CO>[Cl:24][C:22]1[C:21]([O:25][CH3:26])=[CH:20][C:19]([O:27][CH3:28])=[C:18]([NH:17][C:16]([CH2:15][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14][N:5]([CH2:4][C:3]([OH:31])=[O:2])[C:6]2=[O:30])=[O:29])[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68591529{1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester2×

Product 1

HCID 59317691{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An off-white suspension of {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester (Intermediate I) (400 mg, 0.893 mmol) in MeOH (10 ml) is treated with 5 M KOH (5 ml). The resulting white suspension is left to stir at RT overnight to give clear solution. The aqueous reaction mixture is acidified with dilute HCl (1 M) to pH 4 to give a thick white precipitate which is filtered, washed with water and vacuum dried to afford the title compound as pale yellow solid; [M+H]+ 434.

Workup

  1. waitThe resulting white suspension is left
  2. customto give clear solution
  3. customto give a thick white precipitate which
  4. filtrationis filtered
  5. washwashed with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-237ddda454684b4e921beb4893093fab
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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