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

HRID 243203Notes

Reaction equation

HRID 243203 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:13]=[CH:14][C:15]([F:22])=[C:16]2[C:21]=1[NH:20][CH2:19][CH2:18][CH2:17]2)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:24])[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])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157874[(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester2×

Product 1

HCID 68157547[(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl esterYield 555.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of [(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (15 mg, 0.044 mmol) in AcOH (1 mL) was stirred at 100° C. for 2 h, then concentrated in vacuo. A further portion of [(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (90 mg, 0.267 mmol) in AcOH (5 mL) was stirred at 100° C. for 1 h, then concentrated in vacuo. The combined residues were purified by column chromatography (Si—PCC, gradient 30-60% EtOAc in cyclohexane) affording the title compound as a colourless gum (78 mg, 79%). LCMS (Method J): RT 2.19 min [M+H]+ 320

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe combined residues were purified by column chromatography (Si—PCC, gradient 30-60% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-bc4aee55595e462cbd0eb884e3cc5d86
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…