Water → 2-(4-{2-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-1H-1,2,3-triazol-1-yl)propanoic acid

HRID 729486Notes

Reaction equation

HRID 729486 reaction equation
[Br:1][C:2]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[N:18]=[N:19][N:20]([CH:22]([CH3:28])[C:23]([O:25]CC)=[O:24])[CH:21]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[Li+].O.OP([O-])(O)=O.[K+]>CO.C1COCC1>[Br:1][C:2]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[N:18]=[N:19][N:20]([CH:22]([CH3:28])[C:23]([OH:25])=[O:24])[CH:21]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 516951Monobasic potassium phosphateHCID 68828372Ethyl 2-(4-{2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-1H-1,2,3-triazol-1-yl)propanate

Product 1

HCID 578327222-(4-{2-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-1H-1,2,3-triazol-1-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 25 mL round-bottom flask equipped with a magnetic stirbar was added ethyl 2-(4-{2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-1H-1,2,3-triazol-1-yl)propanate (55 mg, 0.11 mmol), 1 mL of THF and 0.5 mL of MeOH. A 1.0 M lithium hydroxide solution in water (0.53 mL, 0.53 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The mixture was poured into a 125 mL separatory funnel containing saturated aqueous KH2PO4 solution (75 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure to yield a beige crystalline solid.

Workup

  1. customInto a 25 mL round-bottom flask equipped with a magnetic stirbar
  2. additionThe mixture was poured into a 125 mL separatory funnel
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customto yield a beige crystalline solid

Sources & evidence

ORD record
ord-e84e0aa595b24d1c8e6ce1edb833dfdf
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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