Potassium Carbonate → N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine

HRID 2238672Notes

Reaction equation

HRID 2238672 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([F:17])=[CH:15][N:14]=[C:13](Cl)[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:19][C@H:20]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:25][C:24]1[CH:23]=[C:22]([C@@H:20]([NH:19][C:13]2[N:12]=[C:11]([C:8]3[N:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]4=[N:10][CH:9]=3)[C:16]([F:17])=[CH:15][N:14]=2)[CH3:21])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 40637894(S)-3-(1-aminoethyl)anilineHCID 862274958-Chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine

Product 1

HCID 68690421N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amineYield 20.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

90 mg of the 8-chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine [125-2] was dissolved in 3 mL of dimethylsulfoxide, then 46.6 mg of 3-[(1S)-1-aminoethyl]aniline and 100 mg of potassium carbonate were added thereto, and stirred at 60° C. for 5 hours. The reaction mixture was cooled back to room temperature, and purified by preparative reversed phase liquid chromatography. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and 25 mg of N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine [125-3] was obtained as a brown oily product.

Workup

  1. temperatureThe reaction mixture was cooled back to room temperature
  2. custompurified by preparative reversed phase liquid chromatography
  3. additionThereto, a saturated aqueous solution of sodium hydrogen carbonate was added
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insolubles were filtered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d05363552c8450aa0ac5dab546a190a
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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