Sodium Hydroxide → HCID 60197771, compound

HRID 1472505Notes

Reaction equation

HRID 1472505 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11](/[CH:21]=[CH:22]/[C:23]([O:25]C)=[O:24])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70655482HCID 70655482, compound

Product 1

HCID 60197771HCID 60197771, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (E)-methyl 3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylate (120 mg, 0.34 mmol, 1.00 equiv) in methanol (15 mL) was added a solution of sodium hydroxide (136 mg, 3.40 mmol, 9.97 equiv) in water (2 mL). The resulting solution was stirred for 2 h at 50° C. in an oil bath, concentrated in vacuo, and diluted with 20 mL of water. The pH value was adjusted to 4-5 with HCl (1M). The resulting solids were collected by filtration, and purified by Prep-HPLC with the following conditions (1#-Waters 2767-2): Column, SunFire Prep C18, 19*150 mm Sum; mobile phase, water with 0.05% TFA and CH3CN (50% CH3CN up to 60% in 8 min, hold 60% in 1 min, up to 100% in 0.1 min, hold 100% in 0.9 min); Detector, UV 220&254 nm. This resulted in 50 mg (43%) of (E)-3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylic acid as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with 20 mL of water
  3. filtrationThe resulting solids were collected by filtration
  4. custompurified by Prep-HPLC with the following conditions (1#-Waters 2767-2)
  5. waitmobile phase, water with 0.05% TFA and CH3CN (50% CH3CN up to 60% in 8 min
  6. customin 1 min
  7. waitup to 100% in 0.1 min
  8. customin 0.9 min
  9. customThis resulted in 50 mg (43%) of (E)-3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylic acid as a white solid

Sources & evidence

ORD record
ord-a343775c067b420d86c91df0352c0156
Source dataset
uspto-grants-2015_04
Patent number
US09012637B2

Reaction notes

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