Hydrochloric Acid → 2-(6-(1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-N-isopropylquinoline-7-carboxamide dihydrochloride

HRID 338864Notes

Reaction equation

HRID 338864 reaction equation
[F:1][C:2]([F:43])([F:42])[CH: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]([C:23](=[O:28])[NH:24][CH:25]([CH3:27])[CH3:26])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.[ClH:44]>C(Cl)Cl.CC(O)C>[ClH:44].[ClH:44].[NH2:34][C@H:31]1[CH2:32][CH2:33][N:29]([CH:3]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([C:10]([C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][C:17]([C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:28])=[CH:18][CH:19]=5)[N:14]=4)=[N:11][N:12]=3)[CH:9]=2)[C:2]([F:43])([F:42])[F:1])[CH2:30]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707421tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(7-(isopropylcarbamoyl)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 867074222-(6-(1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-N-isopropylquinoline-7-carboxamide dihydrochlorideYield 103.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(7-(isopropylcarbamoyl)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.023 g, 0.039 mmol) in DCM (0.5 mL) was added 5 N HCl (0.39 mL, 1.92 mmol) in IPA. The mixture was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure to give 2-(6-(1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-N-isopropylquinoline-7-carboxamide dihydrochloride (0.023 g, 95.7%) as a solid. LCMS APCI (+) m/z 498 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5b4b677afc5542e9a86be4357c6f7493
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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