Ethanol → HCID 56603079, compound

HRID 2043438Notes

Reaction equation

HRID 2043438 reaction equation
C(O)C.[OH-].[Na+].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([NH:15][C:16]2[N:21]=[C:20]([N:22]3[CH:26]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:24]=[N:23]3)[CH:19]=[C:18]([NH:32][C:33]3[CH:38]=[N:37][CH:36]=[CH:35][N:34]=3)[N:17]=2)[CH3:14])=[CH:9][CH:8]=1>O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([NH:15][C:16]2[N:21]=[C:20]([N:22]3[CH:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[N:23]3)[CH:19]=[C:18]([NH:32][C:33]3[CH:38]=[N:37][CH:36]=[CH:35][N:34]=3)[N:17]=2)[CH3:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 67007256HCID 67007256, compound

Product 1

HCID 56603079HCID 56603079, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 ml of ethanol, 1 ml of tetrahydrofuran and 80 μl of 12% sodium hydroxide aqueous solution were added to 35 mg of ethyl (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-1H-pyrazole-4-carboxylate, and the mixture was stirred at room temperature for 18 hours. 160 μl of 12% sodium hydroxide aqueous solution was added thereto, and the mixture was further stirred for 3 hours. Ethanol was distilled off. The obtained residue was diluted with ethanol, and diluted with water, and the pH of the mixture was adjusted to 7 by using 10% hydrochloric acid, the mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 14 mg of the objective compound as white powder.

Workup

  1. stirringthe mixture was further stirred for 3 hours
  2. distillationEthanol was distilled off
  3. additionThe obtained residue was diluted with ethanol
  4. additiondiluted with water
  5. extractionthe mixture was subjected to extraction with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-92d2af7c1bfc46ce9ccf44a05ecfaadd
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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