Hydrochloric Acid → HCID 56838006, compound

HRID 2043433Notes

Reaction equation

HRID 2043433 reaction equation
C(OC[N:10]1[N:14]=[N:13][C:12]([C:15]2[N:20]=[C:19]([NH:21][C@H:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH3:23])[N:18]=[C:17]([NH:31][C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)[CH:16]=2)=[N:11]1)C1C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C@@H:22]([NH:21][C:19]2[N:18]=[C:17]([NH:31][C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)[CH:16]=[C:15]([C:12]3[N:11]=[N:10][NH:14][N:13]=3)[N:20]=2)[CH3:23])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67008050HCID 67008050, compound

Product 1

HCID 56838006HCID 56838006, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

50 mg of (S)-6-[2-(Benzyloxymethyl)-2H-tetrazol-5-yl]-N2-[1-(4-fluoro phenyl)ethyl]-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine was dissolved in 1.5 ml of methanol, and 1.5 ml of 10% hydrochloric acid was added thereto, and the mixture was stirred at 80° C. for hours. The reaction solution was air-cooled to room temperature, and then diluted with ethyl acetate, and the pH of the mixture was adjusted to 4 by using saturated sodium bicarbonate aqueous solution. The organic layer was subjected to extraction, and washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was washed with methanol and filtered and dried under reduced pressure to obtain 15 mg of the objective compound as white powder.

Workup

  1. temperatureThe reaction solution was air-cooled to room temperature
  2. extractionThe organic layer was subjected to extraction
  3. washwashed in turn with water and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washthe obtained residue was washed with methanol
  7. filtrationfiltered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a8b703444967496f9e25b542dd366ea5
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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