Hydrochloric Acid → HCID 71656208, compound

HRID 1428681Notes

Reaction equation

HRID 1428681 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[N:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])[C:10]2=[N:11][C:12]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:14]=[C:9]2[CH:8]=1)(=O)C.[OH-].[Na+].Cl.CCCC(C)C>CCO.CCOC(C)=O.O>[OH:4][CH2:5][CH2:6][C:7]1[N:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[C:10]2=[N:11][C:12]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[N:14]=[C:9]2[CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78922-MethylpentaneHCID 14798Sodium Hydroxide3×HCID 86690331HCID 86690331, compound

Product 1

HCID 71656208HCID 71656208, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(6-(2-acetoxyethyl)-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (step 4) (17 mg, 0.031 mmol) in EtOH (1 ml) at RT was treated with 2M NaOH (0.047 ml, 0.094 mmol) and stirred at RT for 4 hours. Further 2M NaOH (0.047 ml, 0.094 mmol) was added and the mixture was stirred at RT for 16 hours overnight. Further 2M NaOH (0.047 ml, 0.094 mmol) was added and the orange RM was stirred at RT overnight. The resulting mixture was added to water (30 ml) and the pH was adjusted to pH1 by addition of 2M HCl. The aqueous was extracted with DCM (×4) and the combined extracts were passed through a phase separating column and concentrated under reduced pressure to afford an orange oil. The oil was dissolved in EtOAc and an excess of iso-hexane was added. The resulting suspension was sonicated and removed by filtration. The filtrate was concentrated under reduced pressure and the crude product was dissolved in DCM (minimal) and loaded onto a Si 20 mm×20 mm preparative TLC plate. Using a solvent system of 10% MeOH in DCM (200 ml) the TLC plate was eluted and the appropriate strip of Si on the plate was scrapped off the plate. The Si was suspended in 10% MeOH/DCM and sonicated. The suspension was filtered, rinsing the solid with 10% MeOH/DCM. The filtrate was concentrated under reduced pressure to afford the title compound;

Workup

  1. stirringthe mixture was stirred at RT for 16 hours overnight
  2. stirringthe orange RM was stirred at RT overnight
  3. extractionThe aqueous was extracted with DCM (×4)
  4. customseparating column
  5. concentrationconcentrated under reduced pressure
  6. customto afford an orange oil
  7. customThe resulting suspension was sonicated
  8. customremoved by filtration
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. dissolutionthe crude product was dissolved in DCM (minimal)
  11. washwas eluted
  12. customsonicated
  13. filtrationThe suspension was filtered
  14. washrinsing the solid with 10% MeOH/DCM
  15. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42c95eb5b9d945bf9b6a4c2befccb846
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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