Methyl cyanoacetate → HCID 5178717, compound
Reaction equation
ClC1C2SC=CC=2N[C:6](=[O:10])[C:7]=1[C:8]#[N:9].[CH3:14][O:15][C:16]([C:18]1[S:19][CH:20]=[CH:21][C:22]=1[NH2:23])=[O:17].COC(=O)CC#N>>[CH3:14][O:15][C:16]([C:18]1[S:19][CH:20]=[CH:21][C:22]=1[NH:23][C:6](=[O:10])[CH2:7][C:8]#[N:9])=[O:17]Participants
4
Procedure
To prepare compounds of structure (I) with R2 as carbonitrile, and R1 and R3 as defined above, 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carbonitrile, depicted by formula (12), was used as a key intermediate. To prepare this intermediate, methyl-3-amino-thiophene-2-carboxylate was reacted with methylcyanoacetate to yield intermediate 3-(2-cyano-acetylamino)-thiophene-2-carboxylic acid methyl ester, depicted by formula (10). This intermediate was converted to 7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carbonitrile, depicted by formula (11), by reacting with sodium ethoxide, and was then converted into 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carbonitrile, depicted by formula (12), as shown in Scheme 5.
Sources & evidence
- ORD record
- ord-0cb35eab8c96468ba111f52c1b25b398
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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