Hydrochloric Acid → 3-(5-(5-Chloro-2-(((3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

HRID 405216Notes

Reaction equation

Cl.O1CCOCC1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]([F:51])([F:50])[F:49])[CH:42]=3)=[CH:37][CH:36]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[O:22])=[N:19][CH:20]=2)[CH:14]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]([F:51])([F:49])[F:50])[CH:42]=3)=[CH:37][CH:36]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[N:19][CH:20]=2)[CH:14]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 71060116Tert-butyl 3-(5-(5-chloro-2-(((3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710599993-(5-(5-Chloro-2-(((3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoic acid

Procedure

A 4M HCl solution in 1,4-dioxane (3 mL, 12 mmol) was added to a tert-butyl 3-(5-(5-chloro-2-(((3′-(trifluoromethoxy)-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate (49 mg, 0.08 mmol) and the resulting mixture was stirred at room temperature. After 1.5 h the resulting mixture was concentrated in vacuo, triturated with MeOH (0.5 mL) and diethyl ether (5 mL), and filtered to yield the title compound.

Workup

concentrationAfter 1.5 h the resulting mixture was concentrated in vacuo
customtriturated with MeOH (0.5 mL) and diethyl ether (5 mL)
filtrationfiltered

Sources & evidence

ORD record: ord-cb5811ab3d8c45fa8c031e4061b4d183
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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