Methyl 3-amino-2-thiophenecarboxylate → HCID 2807589, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])NC2C=CSC=2C=1Cl)=[O:5])[CH3:2].[CH3:17][O:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][C:25]=1[NH2:26])=[O:20].C(C(C(Cl)=O)C(Cl)=O)C>>[CH3:17][O:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][C:25]=1[NH:26][C:11](=[O:12])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:20]Participants
Procedure
A preferred intermediate in the preparation of compound of structure (I) is 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester, depicted by formula (4) below. To prepare this intermediate, methyl-3-amino-thiophene-2-carboxylate was reacted with ethylmalonyl chloride to yield intermediate 3-(2-ethoxycarbonyl-acetylamino)-thiophene-2-carboxylic acid methyl ester, depicted by formula (1). This intermediate was converted to 7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester, depicted by formula (2), by reacting with sodium ethoxide, and was then converted into 5,7-dihloro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester, depicted by formula (3). Hydrolysis of 5,7-dihloro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester, depicted by formula (3), yielded 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyrdine-6-carboxylic acid ethyl ester, depicted by formula (4) as shown in Scheme 1.
Sources & evidence
- ORD record
- ord-1bf1f085872f47f8bc68e488189f072b
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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