Hydrochloric Acid → HCID 57691227, compound

HRID 219134Notes

Reaction equation

HRID 219134 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]5[CH:29]=[CH:28][C:27]([N:30](C)[C:31](=O)OC(C)(C)C)=[CH:26][CH:25]=5)[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(N(CC)CC)C>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]5[CH:25]=[CH:26][C:27]([NH:30][CH3:31])=[CH:28][CH:29]=5)[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 8471TriethylamineHCID 57691080HCID 57691080, compound

Product 1

HCID 57691227HCID 57691227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl 4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl(methyl)carbamate (0.067 g, 0.13 mmol) was dissolved in MeOH (1.7 mL) and to the solution was added concentrated HCl (0.50 ml, 6.0 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion, the crude mixture was concentrated in vacuo. The solid that remained after concentration was dissolved in MeOH and to the solution was added triethylamine (0.23 ml, 1.6 mmol). The reaction was allowed to stir for 1 h. The crude mixture was concentrated in vacuo. The compound was purified using via flash chromatography, eluting with 5-8% MeOH/NH4OH in DCM to yield 4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-methylbenzenamine as a yellow solid.

Workup

  1. concentrationUpon completion, the crude mixture was concentrated in vacuo
  2. concentrationafter concentration
  3. dissolutionwas dissolved in MeOH and to the solution
  4. stirringto stir for 1 h
  5. concentrationThe crude mixture was concentrated in vacuo
  6. customThe compound was purified
  7. washeluting with 5-8% MeOH/NH4OH in DCM

Sources & evidence

ORD record
ord-6823b75b77544ed1b919776c94ddf290
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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