Sodium Hydroxide → 5-Iodo-6-(2,2,2-trifluoroethoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide
Reaction equation
[I:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[F:18][C:19]([F:28])([F:27])[C:20]1[N:24]=[C:23]([CH2:25][NH2:26])[O:22][N:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CN(C=O)C>[I:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:26][CH2:25][C:23]1[O:22][N:21]=[C:20]([C:19]([F:28])([F:27])[F:18])[N:24]=1)=[O:9]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Iodo-6-(2,2,2-trifluoroethoxy)nicotinic acid (Example 1a, 1 g, 2.88 mmol) was dissolved in DMF (10 mL). C-(3-trifluoromethyl-1,2,4-oxadiazol-5-yl)-methylamine hydrochloride (616 mg, 3.03 mmol), TBTU (981 mg, 3.05 mmol) and N,N-diisopropylethylamine (1.86 g, 2.45 ml, 14.4 mmol) were added. The reaction mixture was stirred overnight, poured into 75 mL 1 M NaOH solution and extracted with i-propyl acetate (2×200 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give a brown oil. The crude material was purified by flash chromatography (silica gel, 50 g, 25% i-propyl acetate in n-heptane) to give the title compound (1.2 g, 84%) as light yellow solid; MS (ESI) 497.0 (M+H)+.
Workup
- extractionextracted with i-propyl acetate (2×200 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customto give a brown oil
- customThe crude material was purified by flash chromatography (silica gel, 50 g, 25% i-propyl acetate in n-heptane)
Sources & evidence
- ORD record
- ord-d30385a0a2024eb58b5a49c76095372c
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629166B2
Reaction notes
Loading…