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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO3
To a solution of 2-oxoindoline-5-carboxylic acid (200 mg, 1.12 mmol) in DMF (3 mL) was added HATU (644 mg, 1.69 mmol) and the reaction mixture was stirred for 30 min at room temperature. After being cooled to 0 C 1-cyclopropyl-4-methylpyrrolidin- 3-amine (174 mg, 1.24 mmol) and DIPEA (0.29 mL, 1.69 mmol) were added successively to the reaction mixture. The reaction was further stirred at room temperature for 2 hrs. Completion of the reaction was confirmed by TLC. After completion, water (30 mL) was added to reaction mixture and product was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine, and dried over sodium sulfate and concentrated under vacuum to get crude product which was purified by column chromatography. The desire compound started eluting at 4% methanol in DCM. Evaporation of the fractions afforded 70 mg of pure racemic compound as a mixture of cis : trans isomer. The cis and trans isomers were separated out using reverse-phase prep. HPLC using 0.1% TFA in ACN and 0.1% TFA in water as mobile phase. Lyophilization of pure fractions afforded the pure title compounds. The yields of the isomers were (18 mg (5.33%) and 23 mg (6.81%) a and LCMS of the isomers were: 1H NMR (400 MHz, MeOD): 7.7 97-6.95 (m, 1H), 4.15 (dd, J = 6 Hz, 1H), 3.60-3.58 (m, 1H), 3.51 (m , 1H), 3.18 (dd, J = 6 Hz, 1H), 2.82- 2.78 (m, 1H), 2.40-2.36 (t, J = 8.4 Hz, 1H), 2.25 2.21 (m, 1H), 1.21-1.20 (m, 3H), 0.53- 0.49 (m, 4H). LCMS (m/z): 300.25 [M+H]+. 1H NMR (400 MHz, MeOD): 7.78-7.76 (m, 2H), 6.98-6.96 (m, 1H), 4.68 (dd, J=5.2 Hz, 1H), 3.61-3.59 (m, 1H), 3.24 (dd, J=5.2 Hz, 1H), 3.12 (dd, J=7.6 Hz, 1H), 2.72 (dd, J=6.4 Hz, 1H), 2.59-2.55 (m, 1H), 2.45 (t, J= 9.2 Hz, 1H), 1.86-1.84 (m, 1H), 0.97-0.95 (m, 3H), 0.54-0.48 (m, 4H). LCMS (m/z): 300.25 [M+H]+.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 102359-00-2.
Reference:
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (102 pag.)WO2016/40508; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem