Hydrochloric Acid → HCID 70984773, compound

HRID 339072Notes

Reaction equation

HRID 339072 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([C:15]1[N:19]3[CH:20]=[C:21]([C@@H:24]([N:26]4[CH2:30][CH2:29][C@H:28]([NH:31]C(=O)OC(C)(C)C)[CH2:27]4)[CH3:25])[CH:22]=[CH:23][C:18]3=[N:17][N:16]=1)[CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].Cl>C(Cl)Cl.CC(O)C>[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([C:15]1[N:19]3[CH:20]=[C:21]([C@@H:24]([N:26]4[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27]4)[CH3:25])[CH:22]=[CH:23][C:18]3=[N:17][N:16]=1)[CH:11]=[CH:10]2)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707549HCID 86707549, compound

Product 1

HCID 70984773HCID 70984773, compoundYield 126.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((S)-1-(3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.203 g, 0.39 mmol) in DCM (1 mL) was added 4 N HCl (1.97 mL, 7.89 mmol) in IPA. The mixture was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure and ether (5 mL) was added. The suspension was stirred at ambient temperature for 10 minutes and the solid formed was collected by filtration to give (S)-1-((S)-1-(3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl) pyrrolidin-3-amine (0.204 g, 98.7%) as solid.

Workup

  1. customThe solvent was removed under reduced pressure and ether (5 mL)
  2. additionwas added
  3. stirringThe suspension was stirred at ambient temperature for 10 minutes
  4. customthe solid formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-44bbbcfb60434c92a4115ff9a4c62cda
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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