Hydrochloric Acid → HCID 67772363, compound

4-Chlorobenzoic acid (0.470 g, 3 mmol), TBTU (0.963 g, 3 mmol) and NMM (0.330 mL, 3 mmol) was mixed in DMF (10 mL). After 10 min at rt was a solution of (S)—N,3-dimethyl-1-(pyrrolidin-1-yl)butan-2-amine (0.426 mg, 2.50 mmol) (for synthesis, see e.g. Synthetic Communications (1994), 24 (10), 1475-81) and NMM (0.430 mL, 3.9 mmol) in DMF (5 mL) added. The resultant mixture was stirred at rt for 16 h. The reaction mixture was washed with Na2CO3 (1M, 2 mL) and concentrated under reduced pressure. The residue was purified by preparative HPLC to give an oily residue. The residue was dissolved in EtOH (5 mL). HCl (1.25 N EtOH solution, 10 mL) and H2O (5 mL) were added and the mixture freezing-dried to give the title compound (600 mg, 58%). Mixture of rotamers: 1H NMR (600 MHz, CD3OD) δ 1.00, 1.10, 1.86-1.98, 2.11, 2.89, 3.18, 3.41, 3.63-3.79, 3.87, 4.68, 7.46, 7.60. HRMS (M+H)+: calculated 309.1733. found 309.1750. XRPD pattern d (Å) 8.4 (med), 7.7 (med), 7.4 (med), 5.0 (vs), 4.31 (str), 4.13 (str), 3.84 (str), 3.46 (str), 3.39 (med), 3.17 (med), 3.00 (med), 2.83 (med).

1. washThe reaction mixture was washed with Na2CO3 (1M, 2 mL)
2. concentrationconcentrated under reduced pressure
3. customThe residue was purified by preparative HPLC
4. customto give an oily residue
5. customthe mixture freezing-dried

ORD record

ord-083a0781d7c6410bacec521251229642

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2