1-(Thien-2-ylcarbonyl)piperazine → 5-Oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carbonitrile
Reaction equation
Cl[C:2]1[C:10]2[C:6](=[CH:7][S:8][CH:9]=2)[NH:5][C:4](=[O:11])[C:3]=1[C:12]#[N:13].[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:11]=[C:4]1[C:3]([C:12]#[N:13])=[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:10]2[C:6](=[CH:7][S:8][CH:9]=2)[NH:5]1Participants
3
Procedure
To yield a compound of structure (II) with R2 as carbonitrile, R3 as thiophene, and R1 as defined above, the intermediate 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carbonitrile, depicted by formula (33), was reacted with piperazin-1-yl-thiophene-2-yl-methanone to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carbonitrile, depicted by formula (34), which was either reacted with an appropriate halide (R1—X) or boronic acid (R1—B(OH)2) to yield target compounds of structure (II) with R2 as carbonitrile, R3 as thiophene, and R1 as defined above, as shown in Scheme 16.
Sources & evidence
- ORD record
- ord-8d94f9b940354829b11093ed20061b75
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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