5-Chloro-2,4-dimethoxyaniline → (2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-ethyl)-carbamic acid tert-butyl ester

HRID 472731Notes

Reaction equation

HRID 472731 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:22][C:23](O)=[O:24])[C:12]1=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[C:29]([O:37][CH3:38])=[CH:30][C:31]([O:35][CH3:36])=[C:32]([CH:34]=1)[NH2:33]>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:22][C:23](=[O:24])[NH:33][C:32]2[CH:34]=[C:28]([Cl:27])[C:29]([O:37][CH3:38])=[CH:30][C:31]=2[O:35][CH3:36])[C:12]1=[O:26])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 668075-Chloro-2,4-dimethoxyanilineHCID 2756025Boc-3-(2-aminoethyl)-1-carboxymethylquinazoline-2,4-dione

Product 1

HCID 59317710(2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-ethyl)-carbamic acid tert-butyl ester

Procedure

This compound is made analogously to Example 1-2 by replacing Intermediate A with [3-(2-tert-butoxycarbonylamino-ethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetic acid and by replacing cyclopentylamine with 5-chloro-2,4-dimethoxyaniline to afford the title compound. The reaction is carried out in DCM.

Sources & evidence

ORD record
ord-23e17dba68404ba49b5c05a4eca9e533
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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