Piperidine → HCID 11454007, compound

Temperature

60 °C

Piperidine (30 μL, 2.0 mmol), Pd2 dba3 (2.7 mg, 0.003 mmol), potassium t-butoxide (59 mg, 0.53 mmol) and 1,3-bis-(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene HCl salt (2.6 mg, 0.006 mmol) are added sequentially to a solution of 3-{[2-(4-chloro-3-trifluoromethyl-phenyl)-benzo[b]thiophen-5-ylmethyl]-amino}-propionic acid tert-butyl ester (72 mg, 0.15 mmol) in 1,4-dioxane (0.8 mL). The mixture is irradiated in a microwave at 100° C. for 1 hour. The reaction is quenched with water and the mixture is concentrated in vacuo. The residue is dissolved in THF and aqueous 2N NaOH (4 mL, 1:1 v/v), and stirred at 60° C. for 3 hours. It is concentrated and purified with preparative LCMS to afford 20 mg of 3-{[2-(4-piperidin-1-yl-3-trifluoromethyl-phenyl)-benzo[b]thiophen-5-ylmethyl]-amino}-propionic acid, which is converted to HCl salt: 1H NMR (400 MHz, CD3OD) δ 8.15-8.00 (m, 4H), 7.87 (s, 1H), 7.63 (d, 1H), 7.57 (d, 1H), 4.48 (s, 2H), 3.44 (t, 2H), 3.03 (t, 4H), 2.89 (t, 2H), 1.90-1.80 (m, 4H), 1.75-1.65 (m, 2H); MS (ES) 463.4 (M+H+).

1. customThe mixture is irradiated in a microwave at 100° C. for 1 hour
2. customThe reaction is quenched with water
3. concentrationthe mixture is concentrated in vacuo
4. dissolutionThe residue is dissolved in THF
5. concentrationIt is concentrated
6. custompurified with preparative LCMS

ORD record

ord-0bb9587da47c4820aa8131c5605964a5

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750021B2