tert-Butyl piperazine-1-carboxylate → 4-(4-Tert-butoxycarbonyl-piperazin-1-yl)-6-oxo-6,7-dihydro-thieno[2,3-b]-pyridine-5-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]2[S:13][CH:14]=[CH:15][C:8]=2[C:7]=1Cl)=[O:5])[CH3:2].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]2[S:13][CH:14]=[CH:15][C:8]=2[C:7]=1[N:27]1[CH2:26][CH2:25][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:29][CH2:28]1)=[O:5])[CH3:2]Participants
3
Procedure
In another method, intermediate 4-chloro-6-oxo-6,7-dihydro-thieno[2,3-b]pyrdine-5-carboxylic acid ethyl ester, depicted by formula (42), was reacted with tert-butyl-1-piperazine carboxylate to yield 4-(4-tert-butoxycarbonyl-piperazin-1-yl)-6-oxo-6,7-dihydro-thieno[2,3-b]-pyridine-5-carboxylic acid ethyl ester, depicted by formula (45). This intermediate was either reacted with an appropriate halide (R1—X) or boronic acid (R1—B(OH)2) to yield intermediate of structure (46), which was deprotected and reacted with an appropriate acid chloride (R3—COCl) or acid (R3—COOH) to yield target compounds of structure (III) with R2 as ethyl carboxylate, and R1 and R3 as defined above, as shown in Scheme 24.
Sources & evidence
- ORD record
- ord-fccadb4529074afb8588ac60300b529f
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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