Formic Acid → (4-{[{3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}(Formyl)Amino]Methyl}Phenyl)Acetic Acid

HRID 2104530Notes

Reaction equation

HRID 2104530 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36]C)=[O:35])=[CH:29][CH:28]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:41])([F:40])[F:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].[CH:44](O)=[O:45]>C(OC(=O)C)(=O)C>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([N:25]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:29][CH:28]=3)[CH:44]=[O:45])[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:39])([F:40])[F:41])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 3939Lithium HydroxideHCID 16718795Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate

Product 1

HCID 86598748(4-{[{3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}(Formyl)Amino]Methyl}Phenyl)Acetic Acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate (0.05 g, 0.09 mmol) in 5 mL of 96% of formic acid and 1 mL of acetic anhydride was heated under reflux for 1 h. Removal of solvent under reduced pressure gave a crude product that was used for the LiOH hydrolysis as described in Example 66. 35 Mg (68%) of the title compound was obtained as a pale yellow solid. MS (ESI) m/z 569; HRMS: calcd for C33H23F3N2O4, 568.1610; found (ESI, [M−H]−), 567.1543.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customRemoval of solvent under reduced pressure
  4. customgave a crude product that

Sources & evidence

ORD record
ord-2ecc2de0d13e4fcdbd05a4474f1d655d
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…