Methanol → HCID 67981052, compound

HRID 2406982Notes

Reaction equation

HRID 2406982 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12]([NH:15][CH:16]([C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=3)[CH2:17][CH2:18][CH3:19])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>C1COCC1>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12]([NH:15][CH:16]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=3)[CH2:17][CH2:18][CH3:19])=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67983601HCID 67983601, compound

Product 1

HCID 67981052HCID 67981052, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Part B: A round bottom flask was charged with (±)-ethyl 4-(1-((5-(4-(trifluoromethyl)phenyl)pyrazin-2-yl)amino)butyl)benzoate (3.96 g, 8.93 mmol), MeOH (70 mL) and THF (70 mL). NaOH aq. 1M (44.6 mL) was then added in one portion and reaction stirred at room temperature for 1 hour and at 50° C. for 2 hours. Reaction mixture was cooled down to room temperature and organic solvents removed under reduced pressure. Water added to dissolve the crude solid and pH adjusted to ca. 4.5 with HCl (aq. 1N). The yellow solid formed was then recovered by filtration with a buchner funnel and dried under high vacuum to provide (±)-4-(1-((5-(4-(trifluoromethyl)phenyl)pyrazin-2-yl)amino)butyl)benzoic acid as a yellow solid (3.23 g, 87.1%). MS (M+1): 416.3.

Workup

  1. customReaction mixture
  2. temperaturewas cooled down to room temperature
  3. customorganic solvents removed under reduced pressure
  4. additionWater added
  5. dissolutionto dissolve the crude solid
  6. customThe yellow solid formed
  7. filtrationwas then recovered by filtration with a buchner funnel
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-62d2eea0500c4635a949823225a21dca
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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