Sodium Hydroxide → 8-Chloro-1-(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[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](O)=[O:20])[CH:14]=1)[C:9](=[O:22])[NH:8][C:7]2=[O:23].ClC1C=CC=C2C=1N(CC1C=CC=C(C(OC)=O)C=1)C(=O)NC2=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[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([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:20])[CH:14]=1)[C:9](=[O:22])[NH:8][C:7]2=[O:23]Participants
6
Reactant 5
Product 1
Procedure
The compound was prepared from 8-chloro-1-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dione (prepared from 8-chloro-1-(3-methoxycarbonylbenzyl)quinazoline-2,4(1H,3H)-dione and NaOH using a procedure similar to those of compound of Examples 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): 11.94 (s, 1H), 8.38 (d, J=4.8 Hz, 2H), 8.05 (d, J=6.6 Hz, 1H), 7.77 (d, J=6.6 Hz, 1H), 7.50-7.20 (m, 5H), 6.66 (t, J=4.8 Hz, 1H), 5.53 (s, 2H), 3.90-3.50 (m, 8H). MS: m/z 477.1 [M+H]+.
Sources & evidence
- ORD record
- ord-ad1b1477402245e9872f5dac2cb7487d
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290460B2
Reaction notes
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