Methyl 5-(chloromethyl)-2-furoate → Methyl 5-((4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)methyl)furan-2-carboxylate
Reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=3[CH:12]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[N:11]([CH2:28]C3CCOC3)[C:10]2=[O:34])[CH:6]=[CH:7][CH:8]=1.ClC[C:39]1[O:43][C:42]([C:44]([O:46][CH3:47])=[O:45])=[CH:41][CH:40]=1>>[C:24]([C:23]1[CH:22]=[CH:21][C:20]([CH:12]2[C:13]3[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][C:18]=3[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:35])([F:36])[F:1])[CH:4]=3)[C:10](=[O:34])[N:11]2[CH2:28][C:39]2[O:43][C:42]([C:44]([O:46][CH3:47])=[O:45])=[CH:41][CH:40]=2)=[CH:27][CH:26]=1)#[N:25]Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared in analogy to 4-(1-(3-(trifluoromethyl)-phenyl)-2,5-dioxo-3-((tetrahydrofuran-3-yl)methyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile (example 25), using methyl 5-(chloromethyl)furan-2-carboxylate as alkylating agent and stirring the reaction mixture at room temperature for 5 d. Yield: 50 mg; ESI mass spectrum [M+H]+=550; Retention time HPLC: 0.94 min (Z011_S03).
Sources & evidence
- ORD record
- ord-94351ac173d74283be4dd6c0cf7dd25d
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115093B2
Reaction notes
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