Trifluoroacetic acid → HCID 66990379, compound

HRID 454739Notes

Reaction equation

HRID 454739 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([CH2:50][CH3:51])[C:16]1[CH:17]=[C:18]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[C:24]([NH:35][C:36]([C:38]3[CH:39]=[N:40][CH:41]=[C:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:43]=3)=[O:37])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1)=O)(C)(C)C>C(Cl)Cl>[CH2:50]([NH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([OH:28])=[O:27])=[C:24]([NH:35][C:36]([C:38]3[CH:39]=[N:40][CH:41]=[C:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:43]=3)=[O:37])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1)[CH3:51]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66991080HCID 66991080, compound

Product 1

HCID 66990379HCID 66990379, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added to a methylene chloride (2.0 mL) solution of the obtained tert-butyl 4-(3-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (0.15 g) at room temperature, followed by stirring at the same temperature for 7 hours and 30 minutes. The solvent was evaporated under reduced pressure, and methanol (3 mL) and dioxane (1 mL) were added to the obtained residue. The pH was adjusted to 13.0 with a 2 mol/L aqueous solution of sodium hydroxide, then to a pH of 4.6 with a 10% aqueous solution of citric acid. The solid substance was collected by filtration to obtain 0.10 g of 4-(3-(ethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a light yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and methanol (3 mL) and dioxane (1 mL)
  2. additionwere added to the obtained residue
  3. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-d9e16e1b61694b77ab42f571f01c5383
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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