Methyl cyanoacetate → HCID 5178717, 화합물

반응식

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]

참가 물질

반응물 3

HCID 7747Methyl cyanoacetate

HCID 89652Methyl 3-amino-2-thiophenecarboxylate

HCID 59702080HCID 59702080, 화합물

생성물 1

HCID 5178717HCID 5178717, 화합물

실험 절차

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.