Sodium Hydroxide → HCID 86690316, compound

HRID 1521896Notes

Reaction equation

HRID 1521896 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:13]=2)[N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])[C:7]1(C1C=CC(C)=CC=1)C1C=CC(C)=CC=1)([CH3:3])[CH3:2].[OH-].[Na+]>CCO.C(OCC)C>[CH:1]([NH:4][CH2:5][C:6]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:13]=2)[N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:7]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131732359HCID 131732359, compound

Product 1

HCID 86690316HCID 86690316, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 7-(7-((isopropylamino)methyl)-2,3-di-p-tolyldi-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (Example 4.1) (53 mg, 0.101 mmol) in EtOH (1 ml) was treated with 2M NaOH (0.151 ml, 0.302 mmol) and stirred at RT for 16 hours. The solvent was removed under reduced pressure and the crude product was dissolved in water and the pH was adjusted to pH 1 using 2M HCl. The mixture was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure to afford an orange solid. The solid was suspended in diethyl ether, sonicated and then filtered, rinsing the filter-cake with diethyl ether (×3). The resultant solid was dried under atmosphere to afford the titled compound as an orange solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude product was dissolved in water
  3. extractionThe mixture was extracted with DCM (×3)
  4. concentrationthe combined organic extracts were concentrated under reduced pressure
  5. customto afford an orange solid
  6. customsonicated
  7. filtrationfiltered
  8. washrinsing the
  9. filtrationfilter-cake with diethyl ether (×3)
  10. customThe resultant solid was dried under atmosphere

Sources & evidence

ORD record
ord-36e0d5529505457faa5c245f855ee958
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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