Propanal → 4-Methoxybenzylamine
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[N:7][C:6]=1[Br:12])[CH3:2].[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21]N=2)[CH:17]=[CH:16][CH:15]=1.[CH:24](=[O:27])CC.[C:28]([CH2:30][C:31]([O:33][CH2:34]C)=O)#N>>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[N:7][C:6]=1[Br:12])[CH3:2].[CH3:24][O:27][C:21]1[CH:16]=[CH:17][C:18]([CH2:23][NH2:14])=[CH:19][CH:20]=1.[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[N:7][C:6]=1[NH:14][CH2:15][C:16]1[CH:28]=[CH:30][C:31]([O:33][CH3:34])=[CH:18][CH:17]=1)[CH3:2]Participants
Procedure
2-Bromo-5-methyl nicotinic acid ethyl ester, depicted by formula 31 in Scheme 12, was used as a starting material to prepare compounds with methyl substitution at 6-position of naphthyridine moiety. This starting material was prepared by condensation of propionaldehyde with ethyl cyanoacetate followed by cyclisation of resulted intermediate as shown in Scheme 12. Amination of 2-bromo-5-methyl nicotinic acid ethyl ester by p-methoxy benzyl amine gave 5-methyl-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester, depicted by formula 32 in Scheme 12, which was then converted into 6-methyl-1-(4-methoxy-benzyl)-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione, depicted by formula 33 in Scheme 12, by reacting with trichloromethyl chloroformate as shown in Scheme 12.
Sources & evidence
- ORD record
- ord-dd75ed9dfc4045739451b99aacd7afec
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361760B2
Reaction notes
Loading…