Methanol → HCID 22667165, compound

HRID 1375793Notes

Reaction equation

HRID 1375793 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=1.CO>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:25]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=1)=[O:27]

Participants

8

Reactant 4

HCID 887MethanolHCID 661742-Amino-5-chloropyridineHCID 94429TriphosgeneHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 22667165HCID 22667165, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (122 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (110 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2-amino-5-chloropyridine (143 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 2 hr. Methanol was added to the reaction solution, and 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 148 mg (yield 82%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  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-47ee0eb3f0404996818ebf790a803eb0
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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