Hydrochloric Acid → (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochloride

HRID 338970Notes

Reaction equation

HRID 338970 reaction equation
[F:1][C:2]([F:43])([F:42])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH:34]C(=O)OC(C)(C)C)[CH2:30]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][C@H:24]([CH3:28])[CH2:25][O:26][CH3:27])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.[ClH:44]>ClCCl>[ClH:44].[ClH:44].[F:42][C:2]([F:1])([F:43])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][C@H:24]([CH3:28])[CH2:25][O:26][CH3:27])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707486tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707487(S)-1-((R)-2,2,2-trifluoro-1-(3-(7-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochlorideYield 162.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.11 g, 0.18 mmol) in dichloromethane (1 mL) was added hydrochloric acid (5-6M in 2-propanol; 9.2 mL, 0.18 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. The solvent was removed under reduced pressure, and the resulting solid was suspended in acetonitrile (3 mL) and stirred at ambient temperature for 5 minutes. The solid formed was collected by vacuum filtration to give the title compound (0.084 g, 77%). LCMS APCI (+) m/z 501 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringstirred at ambient temperature for 5 minutes
  3. customThe solid formed
  4. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-542f557e27c44ed393ed4984b7a92c2f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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