Oxalyl chloride → Methyl 3-(3-(2-bromobenzoyl)ureido)benzoate

HRID 927290Notes

Reaction equation

HRID 927290 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:12](Cl)=[O:13].[NH2:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:6][C:12](=[O:13])[NH:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:5]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 776162-BromobenzamideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 68386708Methyl 3-(3-(2-bromobenzoyl)ureido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-phenyl substituted compound can be prepared as illustrated by the exemplary reaction in Scheme 4. Reaction of 2-bromobenzamide with oxalyl chloride in DCM, followed by addition of methyl 3-aminobenzoate produced methyl 3-(3-(2-bromobenzoyl)ureido)benzoate. Reaction of the benzoate with potassium tert-butoxide in DMF produced 1-(3-methoxycarbonylphenyl)quinazoline-2,4(1H,3H)-dione. Hydrolysis of the ester with NaOH in water-methanol produced 1-(3-carboxyphenyl)quinazoline-2,4(1H,3H)-dione. Coupling of the acid with 2-(piperazin-1-yl)pyrimidine in the presence of coupling agents, such as HATU and DIPEA in DMF, produced the targeted compound 1-(3-(1-(pyrimidin-2-yl)piperazine-4-carbonyl)phenyl)quinazoline-2,4(1H,3H)-dione.

Workup

  1. customas illustrated by the exemplary reaction in Scheme 4

Sources & evidence

ORD record
ord-5e0420d4c93a48038b9db34b8666c21f
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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