Sodium Chloride → HCID 11523767, compound

HRID 605598Notes

Reaction equation

HRID 605598 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=1[F:20].[F:21][C:22]([F:26])([F:25])[CH2:23][NH2:24].[Cl-].[Na+]>CN(C)C=O>[Cl:11][C:4]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=2[F:20])=[C:2]([NH:24][CH2:23][C:22]([F:26])([F:25])[F:21])[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 230182755,7-Dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 11523767HCID 11523767, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine (16 mg, 0.05 mmol) and 2,2,2-trifluoroethylamine (200 mg, 2.0 mmol) in 1 mL of N,N-dimethylformamide is stirred at room temperature for 16 h. A saturated sodium chloride solution is added, and the product is extracted with ethyl acetate. The organic solution is washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated. The residue is chromatographed over silica gel, eluting with a gradient of 20% ethyl acetate in hexanes to 50% ethyl acetate in hexanes. Concentration provides 7-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidin-5-amine as a white solid (16 mg, mp 155-157° C.). MS: m/z 381.0 (M+H).

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic solution is washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed over silica gel
  6. washeluting with a gradient of 20% ethyl acetate in hexanes to 50% ethyl acetate in hexanes
  7. concentrationConcentration

Sources & evidence

ORD record
ord-cbc956e2f1414d048d120961bb6ce6b4
Source dataset
uspto-grants-2011_03
Patent number
US07915266B2

Reaction notes

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