Hydrochloric Acid → HCID 44549037, Verbindung

To a solution of ethyl N-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propyl}glycinate (D93) (50 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 20° C. overnight. The mixture was acidified with aqueous HCl (2 M) to pH 5-6, partitioned between ethyl acetate (25 mL) and water (10 mL). The organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propyl}glycine (E70) (45 mg, TFA salts). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.02 (2H, m), 2.82 (2H, t), 2.95 (2H, t), 3.69 (2H, s), 4.90 (1H, m), 7.23 (1H, t), 7.31 (1H, d), 7.45 (1H, d), 7.82 (1H, d), 7.95 (1H, d), 8.20 (1H, dd), 8.36 (1H, d), 10.85 (1H, s). MS (ES): C24H26ClN4O4 requires 468; found 469.2 (M+H+).

1. custompartitioned between ethyl acetate (25 mL) and water (10 mL)
2. washThe organic phase was washed with water (20 mL) and brine (20 mL)
3. dry with materialdried over anhydrous sodium sulphate
4. customevaporated
5. customto give the crude product, which
6. customwas purified by Mass Directed Auto Prep

ORD-Eintrag

ord-5e1a904044d440b0a8704c868dc92c67

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08217028B2