Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate → Allyl trans-2-[3-(6-Chloro-7-methylthioquinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=[O:14].Br[CH2:16][C:17](=[O:33])[CH2:18][C@H:19]1[C@H:24]([O:25][CH3:26])[CH2:23][CH2:22][CH2:21][N:20]1[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:12][CH3:13])[N:8]=[CH:7][N:6]([CH2:16][C:17](=[O:33])[CH2:18][C@H:19]1[C@H:24]([O:25][CH3:26])[CH2:23][CH2:22][CH2:21][N:20]1[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[C:5]2=[O:14]Participants
3
Procedure
In the manner of Example 4, 0.679 g (0.003 mol) of 6-chloro-7-methylthioquinazolin-4(3H)-one and 1.0 g (0.003 mol) of allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate were converted into the title compound: yield 0.56 g (39%). 1H-NMR(CDCl3) 1.4-2.2 ppm (multiplet, 4H, OCHCH2CH2CH2N), 2.6 (singlet, 3H, SCH3), 2.8-3.4 (multiplet, 4H, NCH2, COCH2CH), 3.4 (singlet, 3H, OCH3), 4.0 (broad singlet, 1H, CHNCO), 4.6 (doublet, 2H, CH2CH=CH2), 5.0 (singlet, 2H, NCH2CO), 5.0-5.5 (multiplet, 2H, CH=CH2), 5.6-6.1 (octet, 1H, CH2 =CH), 7.4 (singlet, 1H, aromatic H), 7.9 (singlet, 1H, N=CH-N), 8.2 (singlet, 1H, aromatic H).
Sources & evidence
- ORD record
- ord-f897a8e3edcb48c796ac061d2bd834e6
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04762838
Reaction notes
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