Trifluoroacetic acid → HCID 117877605, compound

HRID 922485Notes

Reaction equation

HRID 922485 reaction equation
C(OC([N:8]([CH:27]1[CH2:29][CH2:28]1)[CH:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:26])[O:24][CH3:25])[C:14]([CH2:17][CH3:18])=[N:15][CH:16]=1)[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH:27]1([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:26])[O:24][CH3:25])[C:14]([CH2:17][CH3:18])=[N:15][CH:16]=2)[CH3:10])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117877607HCID 117877607, compound

Product 1

HCID 117877605HCID 117877605, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl [3-(5-{1-[(tert-butoxycarbonyl)(cyclopropyl)amino]ethyl}-2-ethylpyridin-3-yl)propyl]carbamate (204 mg) in dichloromethane (1.5 mL) was added trifluoroacetic acid (1.5 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into ice-cooled aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (eluent: chloroform→chloroform/methanol=21/1) to give methyl (3-{5-[1-(cyclopropylamino)ethyl]-2-ethylpyridin-3-yl}propyl)carbamate [REx(113-8)] (142 mg) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. additionThe reaction solution was poured into ice-
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by NH-silica gel column chromatography (eluent: chloroform→chloroform/methanol=21/1)

Sources & evidence

ORD record
ord-75ab3618882648ffaa30bb379205eba5
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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