Chloroform → HCID 46865142, compound

HRID 2043434Notes

Reaction equation

HRID 2043434 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].Cl.Cl.[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[N:15]=[C:14]([NH:25][C@H:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH3:27])[N:13]=1.[CH:35](Cl)(Cl)Cl>>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C@@H:26]([NH:25][C:14]2[N:13]=[C:12]([NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:4])[CH3:35])[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[N:15]=2)[CH3:27])=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 56600586HCID 56600586, compound

Product 1

HCID 46865142HCID 46865142, compound

Conditions

Temperature
0 °C

Procedure

Saturated sodium bicarbonate aqueous solution and chloroform were added to 141 mg of (S)—N4-(2-aminoethyl)-N2-[1-(4-fluorophenyl)ethyl]-N6-(pyrazin-2-yl)pyrimidine-2,4,6-triamine dihydrochloride (Example 76), and the mixture was subjected to extraction. The organic layer washed with brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was dissolved in 3 ml of tetrahydrofuran, and 223 μl of diisopropylethylamine and 23 μl of acetyl chloride were added at 0° C., and the mixture was stirred at 0° C. for 30 minutes. The reaction solution was added with water and subjected to extraction with ethyl acetate. The organic layer washed with brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 95 mg of (S)—N-(2-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}ethyl)acetamide as white powder. The obtained compound was subjected to hydrochlorination using a conventional method to obtain 74 mg of the objective compound as pale yellow powder.

Workup

  1. extractionthe mixture was subjected to extraction
  2. washThe organic layer washed with brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe obtained residue was dissolved in 3 ml of tetrahydrofuran
  6. addition223 μl of diisopropylethylamine and 23 μl of acetyl chloride were added at 0° C.
  7. additionThe reaction solution was added with water
  8. extractionsubjected to extraction with ethyl acetate
  9. washThe organic layer washed with brine
  10. dry with materialdried over magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f1adec4369b447a9c1f266d6274012f
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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