Acetic Acid → HCID 178518183, compound

HRID 1477676Notes

Reaction equation

HRID 1477676 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:10]2)[N:3]=1.C([O-])(=[O:23])C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][C@@H:9]([NH:8][C:4]3[N:5]=[CH:6][NH:7][C:2](=[O:23])[N:3]=3)[CH2:10]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 117839340HCID 117839340, compound

Product 1

HCID 178518183HCID 178518183, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (R)-4-chloro-N-[1-(4-fluorophenyl)pyrrolidin-3-yl]-1,3,5-triazin-2-amine synthesized in Reference Synthesis Example 337, sodium acetate (153 mg, 1.11 mmol), acetic acid (2.0 mL), and water (0.40 mL) were added and the resultant mixture was stirred at 90° C. for 5 hours. After completion of the reaction, the reaction solution was added to saturated sodium bicarbonate aqueous solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure and the obtained solid was washed with ethyl acetate to obtain the title compound (65.0 mg, two step yield 15%).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washthe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-10dbf37392df4646b31d5a0bfa87072b
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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