Cyclopentylamine → N-(5-Chloro-2,4-dimethoxy-phenyl)-2-{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetamide

HRID 472729Notes

Reaction equation

HRID 472729 reaction equation
[Cl:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([O:28][CH3:29])=[C:6]([NH:8][C:9]([CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]([CH2:23]C(O)=O)[C:13]2=[O:27])=[O:10])[CH:7]=1.O=C1N(C2[CH:48]=[CH:47][C:46]([CH2:49][C:50](=[O:60])[NH:51][CH2:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:45][CH:44]=2)C(=O)C2C(=CC=CC=2)N1CC(O)=O.C1(N)CCCC1.ClC1C(OC)=CC(OC)=C(N)C=1>>[Cl:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([O:28][CH3:29])=[C:6]([NH:8][C:9](=[O:10])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]([C:23]3[CH:48]=[CH:47][C:46]([CH2:49][C:50](=[O:60])[NH:51][CH2:52][CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)=[CH:45][CH:44]=3)[C:13]2=[O:27])[CH:7]=1

Participants

5

Reactant 4

HCID 2906CyclopentylamineHCID 668075-Chloro-2,4-dimethoxyanilineHCID 24896589{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acidHCID 68588311{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid

Product 1

HCID 59317686N-(5-Chloro-2,4-dimethoxy-phenyl)-2-{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetamide

Procedure

This compound is made analogously to Example 1-2 by replacing {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid (Intermediate A) with ({2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid) (Intermediate D) and by replacing cyclopentylamine with 5-chloro-2,4-dimethoxy-phenylamine to afford the title compound. The reaction is carried out using DMF as the solvent.

Sources & evidence

ORD record
ord-3a4e43596d004d088cc977bdaf72d118
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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