Hydrochloric Acid → HCID 71657494, compound

HRID 1521891Notes

Reaction equation

HRID 1521891 reaction equation
[CH:1]1([C:4]2[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[C:7]3=[N:8][C:9]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[N:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].O.Cl>CCO>[CH:1]1([C:4]2[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:7]3=[N:8][C:9]([C:19]4[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=4)[N:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86690312HCID 86690312, compound

Product 1

HCID 71657494HCID 71657494, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-(6-cyclopropyl-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (Step 6) (230 mg, 0.464 mmol) in EtOH (4 ml) was treated with 2M NaOH (0.696 ml, 1.392 mmol) and stirred at room temperature for 16 hours. The reaction mixture was added to water (50 ml) and the pH was adjusted to pH 1 by addition of 2M HCl. The resulting suspension was filtered, washed with water (×3) and dried under vacuum. The resultant residue was dissolved in EtOH (minimal) and excess water added. The resultant aqueous was then extracted with DCM (×3), and the organic solvent removed under reduced pressure. The resultant residue was then taken in diethyl ether, sonicated and the solvent removed under reduced pressure. Further diethyl ether was added, sonicated and the solvent removed under reduced pressure. The resultant residue was dissolved in EtOAc (minimal) and excess iso-hexane was added. The resultant suspension was filtered, the filter cake washed with iso-hexane (×4) and dried to afford the titled compound as a pale yellow solid.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashed with water (×3)
  3. customdried under vacuum
  4. dissolutionThe resultant residue was dissolved in EtOH (minimal)
  5. additionexcess water added
  6. extractionThe resultant aqueous was then extracted with DCM (×3)
  7. customthe organic solvent removed under reduced pressure
  8. customsonicated
  9. customthe solvent removed under reduced pressure
  10. additionFurther diethyl ether was added
  11. customsonicated
  12. customthe solvent removed under reduced pressure
  13. dissolutionThe resultant residue was dissolved in EtOAc (minimal)
  14. additionexcess iso-hexane was added
  15. filtrationThe resultant suspension was filtered
  16. washthe filter cake washed with iso-hexane (×4)
  17. customdried

Sources & evidence

ORD record
ord-659a4b12c34346abae4c358def3bcb0f
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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