Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride
[0091 ] In a four necked round bottomed flask, under nitrogen atmosphere, 1000 ml acetonitrile, 49.5 gm of 5,6,7, 7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one.HCl, 55 gm of sodium carbonate and 100 gm of Methyl (R)-2- (4-nitrophenylsulfonyloxy)-2(2- chlorophenyl)acetate were added and the mixture was heated to about 50C. After reaction, reaction mass was filtered, filtrate concentrated and concentrated mass was taken in dichloromethane, washed with water and concentrated under reduced pressure. The oily residue was treated with IPA.HC1 solution in isopropanol (IPA) and filtered to obtain the mixture of isomers as hydrochloride salt. To it sodium bicarbonate solution was added till pH turned alkaline. The product was then extracted in dichloromethane (MDC). The MDC layer was washed with water, dried and distilled to obtain the product as an oily residue. [0092] Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 53.62/46.38% : [0093] Example 2. Methyl (7aS,2’S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydro thieno[3,2-c]-5-pyridin-2-one)acetate [0094] In a four necked round bottomed flask, under nitrogen atmosphere, 150 ml of ethyl acetate-methanol and 70 gm of mixture of isomers (Ratio of (7aS,2’S)/(7aR,2’S)-isomers = 53.62:46.38) was taken and warmed to dissolve, and stirred for 20 hours under room temperature, crystals obtained were filtered and the solid was dried to obtain 52 gm Methyl (S)-2(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one) acetate. Yield = 60%; Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 99.5:0.5. [0095] .H-NMR(DMSO-d6) spectra collected on a BRUKER 400MHz instrument has shown values given in table 2 corresponding to structure of formula II A free base below: [0096] Table 2: No. m- multiplet, s-singlet, d-doublet of doublet. Single crystal analysis data of material conforms to (7aS,2″S)-conl”iguration.
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Reference:
Patent; IPCA LABORATORIES LIMITED; KUMAR, Ashok; SOUDAGAR, Satish Rajanikant; NELLITHANATH, Thankachen Byju; SAHAL, Gaurav; MATHUR, Arpana Prashant; GAWADE, Sanjay Pandurang; BHADRA, Dinesh Kanji; MOJE, Devki; WO2013/1544; (2013); A1;,
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