Hydrochloric Acid → HCID 57691194, compound

HRID 1513729Notes

Reaction equation

HRID 1513729 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]3[N:19]4[CH:20]=[C:21]([C:24]([NH:26][C@H:27]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28]5)=[O:25])[CH:22]=[CH:23][C:18]4=[N:17][N:16]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]3[N:19]4[CH:20]=[C:21]([C:24]([NH:26][C@H:27]5[CH2:31][CH2:30][NH:29][CH2:28]5)=[O:25])[CH:22]=[CH:23][C:18]4=[N:17][N:16]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86630266HCID 86630266, compound

Product 1

HCID 57691194HCID 57691194, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-tert-Butyl 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamido)pyrrolidine-1-carboxylate (0.050 g, 0.096 mmol) was dissolved in methanol (1.5 mL) then added concentrated hydrochloric acid (0.400 ml, 4.8 mmol). The reaction mixture was stirred at room temperature for 5 hours then concentrated under vacuum. The remaining solid was dissolved in methanol (1 mL) then added potassium carbonate (0.062 g, 0.45 mmol). The reaction mixture was stirred at room temperature for 1 hour and concentrated under vacuum. The sample was purified by flash chromatography eluting with 10%-15% 7N ammonia in methanol/dichloromethane to afford (S)-3-((7-methoxyquinolin-4-yloxy)methyl)-N-(pyrrolidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide (0.039 g, 97% yield) as a pale yellow solid.

Workup

  1. concentrationthen concentrated under vacuum
  2. dissolutionThe remaining solid was dissolved in methanol (1 mL)
  3. stirringThe reaction mixture was stirred at room temperature for 1 hour
  4. concentrationconcentrated under vacuum
  5. customThe sample was purified by flash chromatography
  6. washeluting with 10%-15% 7N ammonia in methanol/dichloromethane

Sources & evidence

ORD record
ord-016541ce593a48f38535eb6d9524c2e1
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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