Ethanone, 1-[4-(2-propynylamino)phenyl]- → 4-[[[2-[(2,2-Dimethyl-1-oxopropyl)amino]-3,4-dihydro-4-oxo-6-quinazolinyl]methyl]-2-propynylamino]benzonitrile
Reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)C)=[CH:7][CH:6]=1)[C:2]#[CH:3].Br[CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[NH:20][C:19]2=[O:33].CC(C)(C)C(OC[N:40]1C(=O)C2C(=CC=C(CBr)C=2)N=C1)=O>>[CH3:29][C:28]([CH3:31])([CH3:30])[C:27]([NH:26][C:21]1[NH:20][C:19](=[O:33])[C:18]2[C:23](=[CH:24][CH:25]=[C:16]([CH2:15][N:4]([CH2:1][C:2]#[CH:3])[C:5]3[CH:6]=[CH:7][C:8]([C:11]#[N:40])=[CH:9][CH:10]=3)[CH:17]=2)[N:22]=1)=[O:32]Participants
4
Reactant 3
Product 1
Procedure
In a process analogous to Example 1 by substituting 4-(2-propynylamino)benzonitrile (see Example F) for 1-[4-(2-propynylamino)phenyl]ethanone and N-[6-(bromomethyl)-3,4-dihydro-4-oxo-2-quinazolinyl]-2,2-dimethylpropanamide (Journal of Heterocyclic Chemistry, Vol. 12, pp. 1283-1286 (1975)) for 2,2-dimethylpropanoic acid, [6-(bromomethyl)-4-oxo-3(4H)-quinazolinyl]methyl ester (European patent application No. 204,529) one obtains 4-[[[2-[(2,2-dimethyl-1-oxopropyl)amino]-3,4-dihydro-4-oxo-6-quinazolinyl]methyl]-2-propynylamino]benzonitrile; mp 183°-186° C.
Sources & evidence
- ORD record
- ord-a530846fe5044f5f938ea7188894849e
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857530
Reaction notes
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