Triethylamine → HCID 86673377, compound

HRID 2401237Notes

Reaction equation

HRID 2401237 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[NH:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH2:12])[CH:10]=[C:5]2[CH:4]=1.[Cl:16][C:17]1[C:22]([CH3:23])=[C:21]([C:24]([F:27])([F:26])[F:25])[N:20]=[CH:19][N:18]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[ClH:16].[CH3:23][C:22]1[C:17]([NH:12][CH2:11][C:9]2[CH:10]=[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:14])[F:15])[NH:13][C:6]3=[N:7][CH:8]=2)=[N:18][CH:19]=[N:20][C:21]=1[C:24]([F:27])([F:25])[F:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 178565184-Chloro-5-methyl-6-(trifluoromethyl)pyrimidineHCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 86673377HCID 86673377, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 100 mg, 0.465 mmol), 4-chloro-5-methyl-6-(trifluoromethyl)pyrimidine (ANICHEM CAS425394-59-8, 83 mg, 0.465 mmol) and triethylamine (0.130 mL, 0.929 mmol) were added together in N,N-dimethylformamide (5 mL) and the resulting mixture was stirred at room temperature for overnight. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by trituration in diethyl ether. The resulting solid was dissolved in 1:1 ethyl acetate:methanol and 4M HCl in 1,4-dioxane was added. The mixture was then evaporated under reduced pressure, the resulting residue was triturated again in diethyl ether the mixture was allowed to cool to room temperature and the white solid was collected to give the titled compound as a white solid (175 mgs);

Workup

  1. washwashed with water and brine
  2. customThe organic layer was separated
  3. customdried under magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by trituration in diethyl ether
  6. dissolutionThe resulting solid was dissolved in 1:1 ethyl acetate
  7. additionmethanol and 4M HCl in 1,4-dioxane was added
  8. customThe mixture was then evaporated under reduced pressure
  9. customthe resulting residue was triturated again in diethyl ether the mixture
  10. temperatureto cool to room temperature
  11. customthe white solid was collected

Sources & evidence

ORD record
ord-a25f2c00359b4edfa24d410df38d90f1
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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