Sodium Hydroxide → 8-Chloro-3-(3-(4-(pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](O)=[O:21])[CH:15]=1)[C:7]2=[O:23].ClC1C=CC=C2C=1NC(=O)N(CC1C=CC=C(C(OC)=O)C=1)C2=O.[OH-].[Na+].C(C1C=C(C=CC=1)CN1C2C(=CC=CC=2)C(=O)NC1=O)(O)=O.[N:72]1([C:78]2[N:83]=[CH:82][CH:81]=[CH:80][N:79]=2)[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]1>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:75]3[CH2:76][CH2:77][N:72]([C:78]4[N:79]=[CH:80][CH:81]=[CH:82][N:83]=4)[CH2:73][CH2:74]3)=[O:21])[CH:15]=1)[C:7]2=[O:23]Participants
6
Reactant 5
Product 1
Procedure
The compound was prepared from 8-chloro-3-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dione (prepared from 8-chloro-3-(3-methoxycarbonylbenzyl)quinazoline-2,4(1H,3H)-dione and NaOH using a procedure similar to those of compound of Example 2), and 2-(piperazin-1-yl)pyrimidine using a procedure similar to those described for the synthesis of compound of Example 3. 1H NMR (DMSO-d6): 11.15 (s, 1H), 8.38 (d, J=4.8 Hz, 2H), 7.95 (d, J=7.8 Hz, 1H), 7.82 (d, J=7.5 Hz, 1H), 7.50-7.30 (m, 4H), 7.23 (t, J=7.8 Hz, 1H), 6.67 (t, J=4.8 Hz, 1H), 5.14 (s, 2H), 3.90-3.55 (m, 8H). MS: m/z 477.1 [M+H]+.
Sources & evidence
- ORD record
- ord-f2c8603542764cc6b004415797d97a52
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290460B2
Reaction notes
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