Toluene → (S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethylamine

HRID 243204Notes

Reaction equation

HRID 243204 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:20]2[C:21]3[C:16]([CH2:17][CH2:18][CH2:19]2)=[C:15]([F:22])[CH:14]=[CH:13][C:12]=3[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[F:22][C:15]1[CH:14]=[CH:13][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:20]3[C:21]=2[C:16]=1[CH2:17][CH2:18][CH2:19]3

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 68157547[(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157923(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethylamineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of [(S)-1-(7-fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester (78 mg, 0.244 mmol) in DCM (4 mL) was added TFA (1.3 mL) and the mixture was stirred at RT for 1.5 h. Toluene was added and volatiles were removed under reduced pressure, the resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a colourless gum (49.5 mg, 93%). LCMS (Method B): RT 1.78 min [M+H]+ 220

Workup

  1. customvolatiles were removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in MeOH
  3. washThe cartridge was washed with MeOH
  4. washthe product was eluted with 0.5M NH3/MeOH
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2266f7fb325a494ca5e29059a59225ee
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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