Isobutylamine → HCID 22667203, compound

HRID 1375789Notes

Reaction equation

HRID 1375789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH2:40])[CH:37]([CH3:39])[CH3:38]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:28]([NH:40][CH2:36][CH:37]([CH3:39])[CH3:38])=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 3

HCID 6558IsobutylamineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22667203HCID 22667203, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in chloroform (5 ml) and triethylamine (1 ml), and a solution of triphosgene (104 mg) in dichloromethane was then added to the solution. The mixture was heated under reflux for 5 min. Next, isobutylamine (50 μl) was added to the reaction solution, and the mixture was heated under reflux for 10 min. The reaction solution was purified by chromatography on silica gel by development with chloroform/acetone (4/1). Thus, the title compound was quantitatively obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 10 min
  5. customThe reaction solution was purified by chromatography on silica gel by development with chloroform/acetone (4/1)

Sources & evidence

ORD record
ord-60593d0aebfd41ea89be3af5f636d4c0
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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