Sodium Chloride → HCID 11655616, compound

HRID 1181252Notes

Reaction equation

HRID 1181252 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11](F)=[CH:10][C:9]=2[F:16])=[C:6]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:5]2[CH:23]=[CH:24][N:25]=[C:4]2[N:3]=1.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][OH:31].[H-].[Na+].[Cl-].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:7]([C:8]2[C:9]([F:16])=[CH:10][C:11]([O:31][CH2:30][CH2:29][CH2:28][N:27]([CH3:32])[CH3:26])=[CH:12][C:13]=2[F:14])=[C:6]([NH:17][CH2:18][C:19]([F:21])([F:20])[F:22])[N:5]2[CH:23]=[CH:24][N:25]=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 766463-(Dimethylamino)-1-propanolHCID 11523767HCID 11523767, compound

Product 1

HCID 11655616HCID 11655616, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidin-5-amine (19 mg, 0.05 mmol) and 3-dimethylamino-1-propanol (51 m g, 0.5 mmol) in 0.5 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 20 mg, 0.5 mmol). The mixture is heated at 50° C. for 30 minutes, and cooled to room temperature. A saturated sodium chloride solution is added, and the product is extracted with ethyl acetate. The organic solution is washed with saturated sodium chloride (×3), dried over magnesium sulfate, and concentrated. The residue is chromatographed over silica gel, eluting with a gradient of ethyl acetate to 30% methyl alcohol in ethyl acetate. Concentration provides 7-chloro-6-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyrimidin-5-amine as a tan solid (12 mg, mp 52-55° C.). MS: m/z 464.3 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe product is extracted with ethyl acetate
  3. washThe organic solution is washed with saturated sodium chloride (×3)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel
  7. washeluting with a gradient of ethyl acetate to 30% methyl alcohol in ethyl acetate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-4325aa5cdf07413cb3d1e5fed7c4a38a
Source dataset
uspto-grants-2007_10
Patent number
US07285555B2

Reaction notes

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