Hydrochloric Acid → HCID 178461878, compound

HRID 1187688Notes

Reaction equation

HRID 1187688 reaction equation
C[O:2][CH2:3][CH2:4]OC.Cl.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][C:18]2[N:23]=[C:22]([NH:24][C:25]3[CH:30]=[N:29][CH:28]=[CH:27][N:26]=3)[CH:21]=[C:20]([C:31]3C=C[N:34]=[C:33](F)[CH:32]=3)[N:19]=2)[CH3:16])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18]2[N:19]=[C:20]([C:31]3[CH:32]=[CH:33][N:34]=[C:3]([OH:2])[CH:4]=3)[CH:21]=[C:22]([NH:24][C:25]3[CH:30]=[N:29][CH:28]=[CH:27][N:26]=3)[N:23]=2)[CH3:16])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 56600798HCID 56600798, compound

Product 1

HCID 178461878HCID 178461878, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

1 ml of 1,2-dimethoxyethane and 10% hydrochloric acid were added to 80 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-6-(2-fluoropyridin-4-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine, and the mixture was stirred at 85° C. for 2 hours. 0.5 ml of 10% hydrochloric acid was added thereto, and the mixture was further stirred for 2 hours. The reaction solution was diluted with ethyl acetate and alkalified with a saturated aqueous solution of sodium bicarbonate. The mixture was subjected to extraction, and the obtained organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained solid was washed with diethyl ether and filtrated, and then dried under reduced pressure to obtain 54 mg of the objective compound as white powder.

Workup

  1. stirringthe mixture was further stirred for 2 hours
  2. extractionThe mixture was subjected to extraction
  3. dry with materialthe obtained organic layer was dried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe obtained solid was washed with diethyl ether
  6. filtrationfiltrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-42387b065626470181a019d991b92c18
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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