Ethanamine, 2,2,2-trifluoro- → 5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)-N-(2,2,2-trifluoroethyl)pyridine-2-carboxamide

HRID 341430Notes

Reaction equation

HRID 341430 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[NH2:7][C:8]1[N:13]=[C:12]([N:14]([CH3:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=[C:10]([C:22]2[N:26]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([C:33](OC)=[O:34])=[N:31][CH:32]=3)[O:24][N:23]=2)[N:9]=1>C1(C)C=CC=CC=1>[NH2:7][C:8]1[N:13]=[C:12]([N:14]([CH3:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:11]=[C:10]([C:22]2[N:26]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[O:34])=[N:31][CH:32]=3)[O:24][N:23]=2)[N:9]=1

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 66803428Methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate

Product 1

HCID 668026885-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)-N-(2,2,2-trifluoroethyl)pyridine-2-carboxamideYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2,2,2-trifluoro-ethylamine (39 mg, 395 μmol) in anhydrous toluene (3 mL) was added bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]-octane (DABAL-Me3) (101 mg, 395 μmol). The resulting solution was stirred at 40 C for 1 h. Methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate (prepared in an analogous manner to Example 279, 80 mg, 197 μmol) was then added to the solution and the reaction mixture was stirred for a further 16 h at 80 C. The reaction mixture was quenched with 1M HCl (1 mL), evaporated to dryness and re-dissolved in DCM. The organic solution was washed with water (3×25 mL), dried over magnesium sulfate, evaporated and purified by silica chromatography (50:50 EtOAc:heptane) to afford the title compound as a white solid (40 mg, 43%).

Workup

  1. additionwas then added to the solution
  2. stirringthe reaction mixture was stirred for a further 16 h at 80 C
  3. customThe reaction mixture was quenched with 1M HCl (1 mL)
  4. customevaporated to dryness
  5. dissolutionre-dissolved in DCM
  6. washThe organic solution was washed with water (3×25 mL)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. custompurified by silica chromatography (50:50 EtOAc:heptane)

Sources & evidence

ORD record
ord-4b381d226d064bc5bd4f142f2a03ad91
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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