1-(Thien-2-ylcarbonyl)piperazine → 6-Oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile
Reaction equation
Cl[C:2]1[C:3]2[CH:13]=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].[N:14]1([C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>>[O:10]=[C:6]1[NH:5][C:4]2[S:11][CH:12]=[CH:13][C:3]=2[C:2]([N:17]2[CH2:18][CH2:19][N:14]([C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[O:21])[CH2:15][CH2:16]2)=[C:7]1[C:8]#[N:9]Participants
3
Procedure
To yield a compound of structure (III) with R2 as carbonitrile, R3 as thiophene, and R1 as defined above, the intermediate 4-chloro-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile, depicted by formula (50), was reacted with piperazin-1-yl-thiophene-2-yl-methanone to yield 6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile, depicted by formula (51). The compound of formula (51) was either reacted with an appropriate halide (R1—X) or boronic acid (R1—B(OH)2) to yield the target compounds of structure (III) with R2 as carbonitrile, R3 as thiophene, and R1 as defined above, as shown in Scheme 26.
Sources & evidence
- ORD record
- ord-e1601e7d3fda4f3e9c03c39374583b9d
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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