Hydrochloric Acid → HCID 117843194, compound

HRID 2209158Notes

Reaction equation

HRID 2209158 reaction equation
[CH:1]1([N:4]2[C:8]3[C:9]([O:27][C@@H:28]([C@@H:30]4[CH2:34][C:33](=[O:35])[NH:32][CH2:31]4)[CH3:29])=[N:10][C:11]([C:13]4[CH:21]=[C:20]5[C:16]([C:17]6(OCC[O:23]6)[C:18](=[O:22])[NH:19]5)=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:3][CH2:2]1.Cl>CO>[CH:1]1([N:4]2[C:8]3[C:9]([O:27][C@@H:28]([C@@H:30]4[CH2:34][C:33](=[O:35])[NH:32][CH2:31]4)[CH3:29])=[N:10][C:11]([C:13]4[CH:21]=[C:20]5[C:16]([C:17](=[O:23])[C:18](=[O:22])[NH:19]5)=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117843596HCID 117843596, compound

Product 1

HCID 117843194HCID 117843194, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into the solution of 6′-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one 3G.26 (20 mg) in MeOH (3 mL) was added aqueous HCl (37%, 1 mL). After reflux for 4 h, the solvent was removed, and extracted with ethyl acetate, washed with saturated sodium bicarbonate and brine. After being dried, the solvent was removed and the residue was dissolved in DCM and the desired product was precipitated out by adding hexane. After filtration and vacuum dry, 6-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)indoline-2,3-dione 3.83 (5 mg) was obtained.

Workup

  1. temperatureAfter reflux for 4 h
  2. customthe solvent was removed
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate and brine
  5. customAfter being dried
  6. customthe solvent was removed
  7. dissolutionthe residue was dissolved in DCM
  8. customthe desired product was precipitated out
  9. additionby adding hexane
  10. filtrationAfter filtration and vacuum
  11. customdry

Sources & evidence

ORD record
ord-6c83469f8b36400ab0eea3653b73c5f2
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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