Trifluoroacetic acid → HCID 57530054, compound

HRID 1454238Notes

Reaction equation

HRID 1454238 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][NH:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]([CH3:22])[CH3:21])=[C:15]([O:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:14]=1)C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][N:20]([CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][CH2:10][CH2:9][NH:7][CH3:6])=[O:30])=[CH:14][C:15]=1[O:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68877668HCID 68877668, compound

Product 1

HCID 57530054HCID 57530054, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[4-dimethylaminomethyl-3-(pyridin-3-yloxy)-benzoylamino]-ethyl}-methyl-carbamic acid tert-butylester (250 mg, 0.58 mmol) in CH2Cl2 (3 mL) was added trifluoroacetic acid (1 mL). The reaction was allowed to stir at rt for 16 h and then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), washed with 1 M NaOH (15 mL), dried (Na2SO4), and concentrated under reduced pressure. FCC purification (MeOH/CH2Cl2) provided the desired product (0.13 g, 68%) as a yellow oil. MS (ESI): m/z found, 329.2 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  3. washwashed with 1 M NaOH (15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customFCC purification (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-affddc8db3f24bc0aa7235f0ffdad692
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

Loading…