1,2-Dimethylpropylamine → HCID 22667190, compound

HRID 1008354Notes

Reaction equation

HRID 1008354 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.[CH3:36][CH:37]([NH2:41])[CH:38]([CH3:40])[CH3:39]>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:41][CH:37]([CH3:36])[CH:38]([CH3:40])[CH3:39])=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 3

HCID 117311,2-DimethylpropylamineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22667190HCID 22667190, compoundYield 65%

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 (47 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 1,2-dimethylpropylamine (55 l) was added to the reaction solution, and the mixture was stirred at room temperature for 10 min. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 89 mg (yield 65%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. customThe solvent was removed by distillation under the reduced pressure
  3. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)

Sources & evidence

ORD record
ord-969aef67abbd4348806470d9a965ca09
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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