Triethylamine → HCID 25212019, compound

A solution of dimethyl-(S)-1-piperidin-3-ylmethyl-amine, dihydrochloride (Preparative Example 29, 108 mg, 0.5 mmol) in THF/DMF (3 mL/500 μL) was treated with triethylamine (95 μL, 1.0 mmol) followed by 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (74 mg, 0.25 mmol, as prepared in Example 2 Method B). The reaction mixture was vigorously stirred or 16 h then evaporated and diluted with water (5 mL). The crude reaction mixture was extracted with EtOAc (2×3 mL) which was then washed with a 1 N NaOH solution (2×3 mL), dried over MgSO4, filtered, and evaporated in vacuo to afford product as a colorless solid. The solid was dissolved in a EtOAc/hexanes (1:1) mixture (1 mL), filtered through a PTFE syringe filter, and again evaporated in vacuo to afford product as a colorless solid (31 mg, 31%). LC/MS 5.13 min, [M+1]+ 402.

1. customthen evaporated
2. additiondiluted with water (5 mL)
3. customThe crude reaction mixture
4. extractionwas extracted with EtOAc (2×3 mL) which
5. washwas then washed with a 1 N NaOH solution (2×3 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated in vacuo
9. customto afford product as a colorless solid
10. filtrationfiltered through a PTFE syringe
11. filtrationfilter
12. customagain evaporated in vacuo

ORD record

ord-b4c6a6304c4a41bf8ac9a27b1bec69d1

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029397B2