Toluene → HCID 58494710, compound

HRID 516239Notes

Reaction equation

HRID 516239 reaction equation
[CH3:1][C:2]1[C:3]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12][C:4]=2[CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.C(N(CC)CC)C.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32].C1(C)C=CC=CC=1>ClCCl>[CH2:31]([NH:33][C:34]([N:10]1[C:11]2[C:6](=[CH:5][C:4]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16][C:3]=3[C:2]=2[CH3:1])[CH2:7][CH2:8][CH2:9]1)=[O:35])[CH3:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8022Ethyl isocyanate2×HCID 8471TriethylamineHCID 58494615HCID 58494615, compound

Product 1

HCID 58494710HCID 58494710, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 167 mg of t-butyl 11-methyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 2 ml of dichloromethane were added 0.221 ml of triethylamine and 0.062 ml of ethyl isocyanate, followed by stirring at room temperature for 15 hours. To the reaction mixture were added 3 ml of toluene and 0.062 ml of ethyl isocyanate, followed by heating to 60° C. and stirring for 15 hours. Then, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 200 mg of t-butyl 1-(ethylcarbamoyl)-11-methyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a colorless viscous substance.

Workup

  1. temperatureby heating to 60° C.
  2. stirringstirring for 15 hours
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-f3496b6e645c46b18e8f0c22b952400d
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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