Hydrochloric Acid → HCID 70984649, compound

HRID 339071Notes

Reaction equation

HRID 339071 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 86707548HCID 86707548, compound

Product 1

HCID 70984649HCID 70984649, compoundYield 117.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((R)-1-(3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.197 g, 0.383 mmol) in DCM (1 mL) was added 4 N HCl (1.92 mL, 7.66 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-((R)-1-(3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl) pyrrolidin-3-amine (0.186 g, 92.8%) as solid. LCMS APCI (+) m/z 415 (M+H).

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-2a57c10ad46f4659bb8a30c4bb801f81
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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