Triethylamine → 3-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

HRID 1039365Notes

Reaction equation

HRID 1039365 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[C:13]([CH3:14])=[CH:12][C:11]([NH:15][C:16](=O)[CH2:17][CH2:18][C:19]([O:21]CC)=O)=[C:7]([C:8]([OH:10])=O)[C:6]=1[CH3:25])[CH3:2].C(OC(=O)[C:31]1[C:39](C)=[CH:38][C:37]([NH2:41])=[C:33](C(O)=O)[C:32]=1C)C.[CH2:44]([N:46](CC)CC)[CH3:45].C(C(CC(Cl)=O)C([Cl:56])=O)C>ClCCl>[CH2:1]([O:3][C:4]([C:5]1[C:6]([CH3:25])=[C:7]2[C:11](=[CH:12][C:13]=1[CH3:14])[N:15]=[C:16]([CH2:17][CH2:18][C:19](=[O:21])[NH:46][CH2:44][CH3:45])[N:41]([C:37]1[CH:38]=[CH:39][CH:31]=[CH:32][C:33]=1[Cl:56])[C:8]2=[O:10])=[O:26])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 126858402-Amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acidHCID 218646082-Ethylbutanedioyl dichlorideHCID 865975834-(3-Ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester

Product 1

HCID 115906083-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester: A stirred solution of 4-amino-2,6-dimethylisophthalic acid 1-ethyl ester (0.3 g, 1.26 mmol) and triethylamine (0.355 mL, 2.55 mmol) in dichloromethane (15 mL) at 0° C. is treated with ethyl succinyl chloride (0.199 mL, 1.39 mmol), and the reaction mixture is allowed to warm to room temperature overnight. The reaction mixture is washed with 1 M hydrochloric acid, back-washed with brine and dried over anhydrous MgSO4. The solvent is removed under reduced pressure to afford the title compound, which is used without further purification.

Workup

  1. washThe reaction mixture is washed with 1 M hydrochloric acid
  2. washback-washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-597a5eed3804470c967de9592dc81776
Source dataset
uspto-grants-2013_10
Patent number
US08552015B2

Reaction notes

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