Furan → 4-[4-(Furan-2-carbonyl)-piperazin-1-yl]-6-oxo-6,7-dihydro-thieno[2,3-b]-pyridine-5-carbonitrile
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl[C:7]1[C:8]2[CH:18]=[CH:17][S:16][C:9]=2[NH:10][C:11](=[O:15])[C:12]=1[C:13]#[N:14].[O:19]1C=CC=[C:20]1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:20]([N:24]1[CH2:29][CH2:28][N:27]([C:7]2[C:8]3[CH:18]=[CH:17][S:16][C:9]=3[NH:10][C:11](=[O:15])[C:12]=2[C:13]#[N:14])[CH2:26][CH2:25]1)=[O:19]Participants
4
Procedure
To yield compounds of structure (III) wherein R2 is carbonitrile, R3 is furan, and R1 is as defined above, intermediate 4-chloro-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile, depicted by formula (50), was reacted with 1-(2-furyl)-piperazine to yield 4-[4-(furan-2-carbonyl)-piperazin-1-yl]-6-oxo-6,7-dihydro-thieno[2,3-b]-pyridine-5-carbonitrile, depicted by formula (52). This intermediate was either reacted with an appropriate halide (R1—X) or boronic acid (R1—B(OH)2) to yield target compounds of structure (III) with R2 as carbonitrile, R3 as furan, and R1 as defined above, as shown in Scheme 27.
Sources & evidence
- ORD record
- ord-c44a93c34f4e4502a1007685c5212542
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
Loading…