Methyl 4-aminothiophene-3-carboxylate Hydrochloride → HCID 59702106, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])NC2=CSC=C2C=1Cl)=[O:5])[CH3:2].Cl.[CH3:18][O:19][C:20]([C:22]1[C:26]([NH2:27])=[CH:25][S:24][CH:23]=1)=[O:21].C(C(C(Cl)=O)C(Cl)=O)C>>[CH3:18][O:19][C:20]([C:22]1[C:26]([NH:27][C:11](=[O:12])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:25][S:24][CH:23]=1)=[O:21]Participants
Procedure
A preferred intermediate in the preparation of a compound of formula (II) is 4-chloro-1,2-dihydro-2-oxo-thieno[3,4-b]pyridine-3-carboxylic acid ethyl ester, depicted by formula (25) below. To prepare this intermediate, 4-amino-thiophene-3-carboxylic acid methyl ester hydrochloride, depicted by formula (21), was reacted with ethylmalonyl chloride to yield intermediate 4-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid methyl ester, depicted by formula (22). This intermediate was converted to 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by formula (23) by reacting with sodium ethoxide, and was then converted into 5,7-dihloro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by formula (24). Hydrolysis 5,7-dihloro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by formula (24), yielded 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-3-carboxylic acid ethyl ester, depicted by formula (25), as shown in Scheme 11.
Sources & evidence
- ORD record
- ord-77a6d5c5348d4256b240163b6f54ed2e
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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