Methanol → HCID 22667226, compound

HRID 1375797Notes

Reaction equation

HRID 1375797 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]([CH3:23])[C:17]=1[CH3:24].ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([Br:44])=[CH:40][N:39]=1.CO>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Br:44][C:41]1[CH:42]=[CH:43][C:38]([NH:37][C:29]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[C:17]([CH3:24])[C:18]=2[CH3:23])=[O:35])=[N:39][CH:40]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 706222-Amino-5-bromopyridineHCID 94429TriphosgeneHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 22667226HCID 22667226, compoundYield 41.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (120 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-bromopyridine (192 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/methanol (91/9). The solvent was removed by distillation, and a crystal was precipitated from a minor amount of methanol and a large amount of ether. The crystal was collected by filtration to give 80 mg (yield 41%) 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/methanol (91/9)
  4. customThe solvent was removed by distillation
  5. customa crystal was precipitated from a minor amount of methanol
  6. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-edca48962c374deea5a8216b4ab94385
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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