Triethylamine → N-[[1-methyl-2-(trifluoromethyl)indol-5-yl]methyl]-2-(trifluoromethyl)-pyrimidine-5-carboxamide

2-(Trifluoromethyl)-5-pyrimidinecarboxilic acid (Bio-Farma; 152 mg, 0.789 mmol) was stirred in DCM (10 ml). Oxalyl chloride (0.115 ml, 1.315 mmol) then DMF (0.509 μl, 6.57 μmol) were added. The reaction mixture was then left to stir for 2 hrs under agon. The reaction mixture was then evaporated to dryness and the resulting residues were dissolved in DCM (10 ml). A solution of [(1-methyl-2-trifluoromethylindol-5-yl)methyl]amine (Intermediate 11, 150 mg, 0.657 mmol) in DCM (10 ml) was added followed by triethylamine (0.183 ml, 1.315 mmol). The reaction mixture was then left to stir at room temperature for 1 h. The reaction mixture was quenched with methanol (10 ml) and evaporated to dryness. The resulting residues were then partitioned between ethyl acetate and a 1M solution of citric acid. The organic layer was collected, dried (MgSO4), filtered and the solvent removed. The resulting residues were purified by MDAP and evaporated to dryness to give the title compound (90 mg);

1. waitThe reaction mixture was then left
2. customThe reaction mixture was then evaporated to dryness
3. dissolutionthe resulting residues were dissolved in DCM (10 ml)
4. waitThe reaction mixture was then left
5. stirringto stir at room temperature for 1 h
6. customThe reaction mixture was quenched with methanol (10 ml)
7. customevaporated to dryness
8. customThe resulting residues were then partitioned between ethyl acetate
9. customThe organic layer was collected
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customthe solvent removed
13. customThe resulting residues were purified by MDAP
14. customevaporated to dryness

ORD record

ord-3288fcc6a1734ce99731a3ad4644fb10

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377941B2