Quinazolinedione → 1-(2-(4-(Pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione

HRID 927303Notes

Reaction equation

HRID 927303 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[NH:9][C:8]1=[O:18])(O)=[O:2].N1C2C(=CC=CC=2)C(=O)NC1=O.BrCC1C=CC=CC=1C(OC)=O.COC(C1C=C(C=CC=1)CN1C2C(=CC=CC=2)C(=O)NC1=O)=O.[N:70]1([C:76]2[N:81]=[CH:80][CH:79]=[CH:78][N:77]=2)[CH2:75][CH2:74][NH:73][CH2:72][CH2:71]1>>[N:77]1[CH:78]=[CH:79][CH:80]=[N:81][C:76]=1[N:70]1[CH2:75][CH2:74][N:73]([C:1]([C:4]2[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=2[CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][C:8]2=[O:18])=[O:2])[CH2:72][CH2:71]1

Participants

6

Reactant 5

HCID 64048QuinazolinedioneHCID 887471-(2-Pyrimidinyl)piperazineHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68388893HCID 68388893, compoundHCID 683890971-(2-carboxybenzyl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 683889491-(2-(4-(Pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione

Procedure

The title compound was prepared from 1-(2-carboxybenzyl)quinazoline-2,4(1H,3H)-dione (prepared from quinazoline-2,4(1H,3H)-dione and methyl 2-(bromomethyl)benzoate using a procedure similar to those used for compounds of Example 1 and 2), and 2-(piperazin-1-yl)pyrimidine using a procedure similar to that described for the synthesis of compound of Example 3. 1H NMR (DMSO-d6): 11.76 (s, 1H), 8.40 (d, J=4.8 Hz, 2H), 8.03-8.00 (m, 1H), 7.70-7.50 (m, 1H), 7.35-7.00 (m, 6H), 6.68 (t, J=4.8 Hz, 1H), 5.25 (s, 2H), 4.10-3.60 (m, 8H). MS: m/z 443.2 [M+H]+.

Sources & evidence

ORD record
ord-845fb353a42c463a829af9e6f1ea5065
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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