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

HRID 243217Notes

Reaction equation

HRID 243217 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][CH:19]2[CH3:22])=[C:15]([F:23])[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:23][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][CH:19]3[CH3:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 68156902[(S)-1-(7-Fluoro-4-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157756(S)-1-(7-Fluoro-4-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethylamineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of [(S)-1-(7-fluoro-4-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester (24.2 mg, 0.0726 mmol) in DCM (4 mL) was added TFA (0.8 mL) and the mixture was stirred at RT for 16 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 (15.8 mg, 93%). LCMS (Method B): RT 1.98 min [M+H]+ 234

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-82264a75c147460e8816af2fbd1bb221
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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