Hydrochloric Acid → HCID 57691194, compound

HRID 219163Notes

Reaction equation

HRID 219163 reaction equation
C1(NC(C2C=CC3N(C(COC4C5C(=CC(OC)=CC=5)N=CC=4)=NN=3)C=2)=O)CC1.[CH3:30][O:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([O:42][CH2:43][C:44]3[N:48]4[CH:49]=[C:50]([C:53]([NH:55][C@H:56]5[CH2:60][CH2:59][N:58]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH2:57]5)=[O:54])[CH:51]=[CH:52][C:47]4=[N:46][N:45]=3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:30][O:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([O:42][CH2:43][C:44]3[N:48]4[CH:49]=[C:50]([C:53]([NH:55][C@H:56]5[CH2:60][CH2:59][N:58]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH2:57]5)=[O:54])[CH:51]=[CH:52][C:47]4=[N:46][N:45]=3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1.[CH3:30][O:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([O:42][CH2:43][C:44]3[N:48]4[CH:49]=[C:50]([C:53]([NH:55][C@H:56]5[CH2:60][CH2:59][NH:58][CH2:57]5)=[O:54])[CH:51]=[CH:52][C:47]4=[N:46][N:45]=3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57690926N-cyclopropyl-3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamideHCID 86630266HCID 86630266, compound

Product 2

HCID 57691194HCID 57691194, compoundYield 194.2%HCID 86630266HCID 86630266, compound

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 was prepared as previously described for N-cyclopropyl-3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide. (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. MS (ESI pos. ion) m/z: 419.2 (MH+).

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-768aeabccfdd42bb82361f6eba6cf1ac
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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