Hydrochloric Acid → [5-(2-Ethylaminomethyl-4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester, dihydrochloride

HRID 554659Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH3:25])[CH:11]=1)[CH3:2].[ClH:34]>CCOC(C)=O.O1CCOCC1>[ClH:34].[ClH:34].[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=2[CH2:22][NH:23][CH2:24][CH3:25])[CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To (5-{2-[(N-tert-butoxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.375 g, 0.8 mmol) in EtOAc (4 mL) was added 4N HCl in 1,4-dioxane (0.8 mL), and the reaction was stirred at 50° C. for 1 hour. Additional 4N HCl in 1,4-dioxane (0.8 mL) was added, and the reaction was stirred for 1 hour at 70° C. The mixture was concentrated to give [5-(2-ethylaminomethyl-4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester, dihydrochloride.

Workup

stirringthe reaction was stirred for 1 hour at 70° C
concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-e57cf283ebc14618be9dcb9a9324ee95
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049015B2

Reaction notes

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