Sodium Hydroxide → HCID 68388416, compound

To a solution of 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (100 mg, 0.306 mmol) in 1,2-dichloroethane (DCE) (2 mL) were added ethyl 2-formyloxazole-4-carboxylate (67.4 mg, 0.398 mmol) and sodium triacetoxyborohydride (97 mg, 0.460 mmol), and the mixture was stirred at room temperature for 18 h. The mixture was quenched with water (2 mL) and extracted with DCM (3×). The extract was dried (Na2SO4) and concentrated. The residue was dissolved in methanol (2.0 mL) and sodium hydroxide (1 mL, 1.0 mmol) was added. The mixture was stirred at room temperature for 3 h and concentrated. The residue was treated with methanol and filtered. The filtrate was purified using reverse-phase HPLC under the acidic conditions to a TFA salt of the product. The TFA salt was treated with ACN (1 mL) and 1NHCl (0.5 mL) and concentrated. The residue was dried under vacuum to give 75 mg of product (HCl salt) as off-white solid. MS: (M+H)+=356.2. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.42 (q, 1H), 1.54-1.85 (m, 3H), 2.10-2.30 (m, 3H), 2.60 (ddd, J=10.36, 6.69, 3.66 Hz, 1H), 3.04 (dt, J=7.58, 4.04 Hz, 1H), 3.72-3.86 (m, 2H), 4.69 (s, 2H), 7.11-7.44 (m, 5H), 8.60-8.78 (m, 1H).

1. customThe mixture was quenched with water (2 mL)
2. extractionextracted with DCM (3×)
3. dry with materialThe extract was dried (Na2SO4)
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in methanol (2.0 mL)
6. stirringThe mixture was stirred at room temperature for 3 h
7. concentrationconcentrated
8. additionThe residue was treated with methanol
9. filtrationfiltered
10. customThe filtrate was purified
11. additionThe TFA salt was treated with ACN (1 mL) and 1NHCl (0.5 mL)
12. concentrationconcentrated
13. customThe residue was dried under vacuum

ORD record

ord-0b36e4085c2740bb9e488938edb839ce

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853408B2