Triethylamine → HCID 57606122, Verbindung

A suspension of (S)-(−)-aminoquinuclidine dihydrochloride (55 mg, 0.275 mmol) in dichloromethane (1 mL) as treated with triethylamine (53 μL, 0.55 mmol) followed by 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (74 mg, 0.25 mmol) and the reaction mixture allowed to stir for 20 hr. After this time, the reaction mixture was evaporated and the residue partitioned between EtOAc (5 mL) and a 1 N HCl solution (10 mL). The aqueous portion was then basified to pH˜10-12 with a 1N NaOH solution. The aqueous portion was then extracted with EtOAc (10 mL) which was then washed with a brine solution (10 mL), dried over MgSO4, filtered, and evaporated in vacuo to afford product as a colorless solid (38 mg, 40%). 1H NMR (CDCl3) 1.50-1.62 (m, 1H), 1.70-1.88 (m, 3H), 2.08-2.12 (m, 2H), 2.37 (d, J=1.3, 3H), 2.72-3.10 (m, 5H), 3.44 (ddd, J=14.0, 9.7, 2.2, 1H), 4.14-4.22 (m, 1H), 6.56 (br d, J=7.0, 1H), 7.49 (d, J=4.0, 1H), 7.56 (d, J=4.0, 1H). 19F NMR −63.13. LC/MS 4.63 min, [M+1]+386.

1. customAfter this time, the reaction mixture was evaporated
2. customthe residue partitioned between EtOAc (5 mL)
3. extractionThe aqueous portion was then extracted with EtOAc (10 mL) which
4. washwas then washed with a brine solution (10 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated in vacuo

ORD-Eintrag

ord-9dea5611f59243a7856da1b2e7a0eab6

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09029397B2