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Trifluoroacetic acid → 5-{[2-(Methylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623789
Notes
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Reaction equation

HRID 1623789 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[O:28])[CH:14]=1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][NH:2][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([CH:14]=1)[C:27]([NH:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 681081751,1-Dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate

Product 1

HCID 699367815-{[2-(Methylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
30 °C

Procedure

To the solution of 1,1-dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate (may be prepared as described in Description 75; 140 mg, 0.17 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (3.0 ml, 38.9 mmol) dropwise. After stirring at 30° C. for 2 h, the pH of the solution was adjusted to 7-8 by adding aqueous NaHCO3 solution. The mixture was extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over Na2SO4, and concentrated to obtain a crude product. The crude product was purified by prep-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*30 mm; A: 0.04% NH3.H2O/water, B: CH3CN; 0-6.0 min, 30%-55%; 6-12 min, 95%, RT=7.3 min) to yield the title compound as a white solid. 20 mg.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was purified by prep-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*30 mm
  7. custom0-6.0 min, 30%-55%

Sources & evidence

ORD record
ord-639af7fb18ec4474a8f7c8bc28f4ce95
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes