[(S)-1-(5-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(7-Fluoro-4-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 243216Notes

Reaction equation

HRID 243216 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:13]=[CH:14][C:15]([F:23])=[C:16]2[C:21]=1[NH:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:25])[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])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157423[(S)-1-(5-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68156902[(S)-1-(7-Fluoro-4-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl esterYield 40.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(5-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (63.6 mg, 0.181 mmol) in AcOH (5 mL) was stirred at 80° C. for 2.5 h, then concentrated in vacuo. The residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane) affording the title compound as a colourless gum (24.2 mg, 40%) LCMS (Method B): RT 2.45 min [M+H]+ 334

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-27882274dafd4066a6a4aeb1e19d7473
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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