Trifluoroacetic acid → HCID 71059851, compound

HRID 405127Notes

Reaction equation

HRID 405127 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH2:39][CH2:40][C:41]([O:43]C(C)(C)C)=[O:42])=[O:37])=[N:34][CH:35]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[O:37])=[N:34][CH:35]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060082HCID 71060082, compound

Product 1

HCID 71059851HCID 71059851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat TFA (0.09 mL, 1.15 mmol) was added to a DCM solution (1 mL) of tert-butyl 3-(5-(2-(((3′,4′-dichloro-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate (44 mg, 0.08 mmol). After 16 h the resulting mixture was concentrated in vacuo, dissolved in DCM and 1 N HCl in diethyl ether was added. The resulting solution was concentrated in vacuo and the DCM/HCl process was repeated 2×. The resulting solid was characterized as the corresponding HCl salt of the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated in vacuo
  2. dissolutiondissolved in DCM
  3. addition1 N HCl in diethyl ether was added
  4. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-20cde158a06147b090669a9b8e0a3e03
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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