1-(Thien-2-ylcarbonyl)piperazine → HCID 59699584, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:17])[NH:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[N:18]1([C:24]([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:17])[NH:8][C:9]2[C:14]([C:15]=1[N:21]1[CH2:22][CH2:23][N:18]([C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[O:25])[CH2:19][CH2:20]1)=[CH:13][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]Participants
Procedure
The starting materials for this synthesis was 4-aminopyridine which was protected by boc group and converted to 4-tert-butoxycarbonylamino-nicotinic acid, depicted as formula 35 in Scheme 15, by ortholithiation followed by quenching with dry ice. This intermediate was reacted with trichloromethyl chloroformate to yield 1H-pyrido[4,3-d][1,3]oxazine-2,4-dione, depicted by formula 36 in Scheme 15, which was then converted to 4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester, depicted by formula 37 in Scheme 15. The reaction of 4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester with piperazine-1-yl-thiophene-2-yl-methanone gave 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester, depicted by formula 38 in Scheme 15, which was reacted with corresponding alkyl halides (R—X) to yield 1-N-substituted-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl esters as shown in Scheme 15.
Sources & evidence
- ORD record
- ord-2bdd2d936b8149b9a070b11a3b5f3d20
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361760B2
Reaction notes
Loading…