Hydrochloric Acid → HCID 71004817, compound

HRID 339028Notes

Reaction equation

HRID 339028 reaction equation
[CH3:1][C@:2]1([NH:34]C(=O)OC(C)(C)C)[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[C:24]([O:32][CH3:33])[CH:25]=[C:26]([F:31])[CH:27]=5)[N:22]=4)=[N:19][N:20]=3)[CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:1][C@:2]1([NH2:34])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[C:24]([O:32][CH3:33])[CH:25]=[C:26]([F:31])[CH:27]=5)[N:22]=4)=[N:19][N:20]=3)[CH:17]=2)[C:8]([F:10])([F:9])[F:11])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707526HCID 86707526, compound

Product 1

HCID 71004817HCID 71004817, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(6-fluoro-8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.900 g, 1.57 mmol) in DCM (8 mL) was added 4M HCl in dioxane (2 mL) and the reaction stirred for 2.5 hours. The reaction was diluted DCM (100 mL) and washed with saturated Na2CO3 (25 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by normal phase chromatography (5% [10% NH4OH]/DCM) to give (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(6-fluoro-8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine (0.690 g, 1.45 mmol, 92.8% yield) MS APCI (+) m/z 475 (M+1) detected.

Workup

  1. washwashed with saturated Na2CO3 (25 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by normal phase chromatography (5% [10% NH4OH]/DCM)

Sources & evidence

ORD record
ord-53ffde59d2f344ec81fb1fd855203c7c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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