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

2-Chloro-pyrimidine-5-Carboxylic acid (209 mg, 1.317 mmol) was stirred in dichloromethane (20 ml). Oxalyl chloride (0.210 ml, 2.394 mmol) then DMF (4.63 μl, 0.060 mmol) was added. The reaction mixture was then left to stir for 2 h under Argon gas. The reaction mixture was then evaporated to dryness and the resulting residues were then dissolved in dichloromethane (20 ml). A solution of {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 300 mg, 1.197 mmol) in DCM (10 mL) was added then triethylamine (0.500 ml, 3.59 mmol) was added. The reaction mixture was then left to stir at room temperature for 24 h. The reaction mixture was evaporated to dryness. The resulting residues where then partitioned between 2M HCl (50 ml) and ethyl acetate (50 ml). The organic layer was collected, dried (MgSO4), filtered and the solvent was removed. The resulting residues where then purified on the MDAP to give the title compound (240 mg);

1. waitThe reaction mixture was then left
2. customThe reaction mixture was then evaporated to dryness
3. dissolutionthe resulting residues were then dissolved in dichloromethane (20 ml)
4. waitThe reaction mixture was then left
5. stirringto stir at room temperature for 24 h
6. customThe reaction mixture was evaporated to dryness
7. customThe resulting residues where then partitioned between 2M HCl (50 ml) and ethyl acetate (50 ml)
8. customThe organic layer was collected
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customthe solvent was removed
12. customThe resulting residues where then purified on the MDAP

ORD record

ord-539a5be6b2534249aa24f7b10d2bbacb

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377941B2