Quinazolinedione → HCID 68388750, compound

HRID 927308Notes

Reaction equation

HRID 927308 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[NH:11][C:10]1=[O:20])([OH:3])=O.N1C2C(=CC=CC=2)C(=O)NC1=O.BrCCC1C=C(C=CC=1)C(OC)=O.[N:49]1([C:55]2[N:60]=[CH:59][CH:58]=[CH:57][N:56]=2)[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>>[N:56]1[CH:57]=[CH:58][CH:59]=[N:60][C:55]=1[N:49]1[CH2:54][CH2:53][N:52]([C:1]([C:4]2[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][C:10]2=[O:20])=[O:3])[CH2:51][CH2:50]1

Participants

5

Reactant 4

HCID 64048QuinazolinedioneHCID 887471-(2-Pyrimidinyl)piperazineHCID 10586288165803-79-2HCID 68388719HCID 68388719, compound

Product 1

HCID 68388750HCID 68388750, compound

Procedure

The compound was prepared from 1-(3-carboxyphenethyl)quinazoline-2,4(1H,3H)-dione (prepared from quinazoline-2,4(1H,3H)-dione and methyl 3-(2-bromoethyl)benzoate using a procedure similar to those used for Examples 1 and 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): 11.54 (s, 1H), 8.37 (d, J=4.8 Hz, 2H), 7.78 (dd, J=7.8 and 1.5 Hz, 1H), 7.73 (t, J=6.9 Hz, 1H), 7.52 (d, J=7.2 Hz, 1H), 7.35-7.22 (m, 5H), 6.66 (t, J=4.7 Hz, 1H), 4.28 (t, J=7.5 Hz, 2H), 3.80-3.20 (m, 8H), 2.95 (t, J=7.4 Hz, 1H). MS: m/z 457.4 [M+H]+.

Sources & evidence

ORD record
ord-007a42198f364dec879a0027655473d5
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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