Hydrochloric Acid → (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochloride

HRID 338895Notes

Reaction equation

HRID 338895 reaction equation
[CH3:1][C@:2]1([NH:35]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:31][CH:32]([CH3:34])[CH3:33])[CH:25]=[CH:26][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.[ClH:43].O1CCOCC1.C(OCC)C>C(Cl)Cl>[ClH:43].[ClH:43].[CH3:1][C@:2]1([NH2:35])[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:31][CH:32]([CH3:33])[CH3:34])[CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[N:19][N:20]=3)[CH:17]=2)[C:8]([F:10])([F:11])[F:9])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 86707436tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707437(S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (1.30 g, 2.22 mmol) in DCM (20 mL) was added 4N HCl in dioxane (5.56 mL, 22.2 mmol). The reaction mixture was stirred at ambient temperature for 3 hours. Diethyl ether (100 mL) was added to the reaction mixture. The suspension was stirred for 10 min. The solid was collected by filtration to give (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochloride (1.20 g, 97%). MS APCI (+) m/z 485 (M+1) detected. Specific rotation: [α]20D=−2.14° (c=0.97, MeOH).

Workup

  1. stirringThe suspension was stirred for 10 min
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-2f5483f64d604b359c00867fedc6d4a9
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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