1,2-Benzenedicarboxylic acid, 3-amino-, hydrochloride (1:1)

off-white to yellow-beige crystalline powder

1) 1) 3-nitrophthalic acid (lOOgm) and 10percent Pd/C (3.2 gm) in ethanol (600ml) was charged in autoclave and hydrogen pressure of 4.0 kg applied for 3.0 hr at 20-25 °C in autoclave. The reaction mass was cooled to 20°C and filtered through hyflo bed. The filtrate was distilled under reduced pressure and to the residue acetone was charged. The reaction mass was cooled to 10°C and followed by addition of conc., hydrochloric acid and stirred. The solvent was removed under reduced pressure and acetonitrile was added. The reaction mass was cooled to 10°C and precipitated solid was filtered. The product was dried at 45-50°C under vacuum for 6 hr to obtain 65.0gm of 3-aminophthalic acid hydrochloride salt.The compound of formula VII 0. 55mol, and 37percent concentrated hydrochloric acid was added 500mL one-neck flask 1L, 25 ° C was stirred for 15h, the water distilled off under reduced pressure, slurried with 300mL tetrahydrofuran 10min, the solvent was distilled off under reduced pressure was repeated twice to give an off-white solid 120g, Karl Fischer determination of water 0.5percent. This solid was added to a 2L four-neck flask, was added acetic anhydride 1. 2L, 100 ° C 15h reaction, acetic anhydride was distilled off under reduced pressure, cooling the residue was added 200 mL of methyl tert-butyl ether, heating 10min, filtered, washed with methyl tert-butyl ether was washed with 20mL solid was filtered, the filter cake was dried in vacuo at 40 ° C 5H, 94g of off-white solid, a yield of 83.3percent.To a mixture of 3-amino phthalic acid hydrochloride (0.144 g, 0.664 mmol) and (S)-5-aminopiperidin-2-one hydrochloride (0.100 g, 0.664 mmol) in dry DMF (2.2 mL) was added triethylamine (0.933 mL, 6.64 mmol) and the reaction mixture was heated at 80 °C over 18 h. The crude mixture was quenched by the addition of a saturated aqueous NaHCO3 solution (30 mL) and extracted using DCM (3x20 mL). Combined organic phases were dried over MgSO4, filtered and concentrated. The crude residue was purified by preparative reverse phase HPLC to give the desired product 30 (0.08 g, 47percent) as an off-white powder. 1H NMR (400 MHz, DMSO) delta 7.56 (s, 1H), 7.42 (dd, J = 7.7, 7.7 Hz, 1H), 6.94 (m, 2H), 6.48 (br s, 2H), 4.32 (m, 1H), 3.60 (app t, J = 11.3 Hz, 1H), 3.23 - 3.02 (m, 1H), 2.62 - 2.42 (obsc m, 1H), 2.42 - 2.21 (m, 2H), 1.86 (m, 1H). MS (ESI) m/z calcd for C13H14N3O3 [M+H]+ 260.3, found: 260.7.The compound of formula VII 0. 55mol, and 37percent concentrated hydrochloric acid was added 500mL one-neck flask 1L, 25 ° C was stirred for 15h, the water distilled off under reduced pressure, slurried with 300mL tetrahydrofuran 10min, the solvent was distilled off under reduced pressure was repeated twice to give an off-white solid 120g, Karl Fischer determination of water 0.5percent. This solid was added to a 2L four-neck flask, was added acetic anhydride 1. 2L, 100 ° C 15h reaction, acetic anhydride was distilled off under reduced pressure, cooling the residue was added 200 mL of methyl tert-butyl ether, heating 10min, filtered, washed with methyl tert-butyl ether was washed with 20mL solid was filtered, the filter cake was dried in vacuo at 40 ° C 5H, 94g of off-white solid, a yield of 83.3percent.A stirred solution of The compound of formula VII 0. 55mol, and 37percent concentrated hydrochloric acid was added 500mL one-neck flask 1L, 25 ° C was stirred for 15h, the water distilled off under reduced pressure, slurried with 300mL tetrahydrofuran 10min, the solvent was distilled off under reduced pressure was repeated twice to give an off-white solid 120g, Karl Fischer determination of water 0.5percent. This solid was added to a 2L four-neck flask, was added acetic anhydride 1. 2L, 100 ° C 15h reaction, acetic anhydride was distilled off under reduced pressure, cooling the residue was added 200 mL of methyl tert-butyl ether, heating 10min, filtered, washed with methyl tert-butyl ether was washed with 20mL solid was filtered, the filter cake was dried in vacuo at 40 ° C 5H, 94g of off-white solid, a yield of 83.3percent.Into a 500 ml_ round bottom flask equipped with a magnetic stir bar was placed Step 1. Into a 500 mL round bottom flask equipped with a magnetic stir bar was placed

Molecular Weight:217.60
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:217.0141854
Monoisotopic Mass:217.0141854
Topological Polar Surface Area:101
Heavy Atom Count:14
Complexity:228
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes