Triethylamine → HCID 23118609, compound

HRID 1348816Notes

Reaction equation

HRID 1348816 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])=[CH:18][C:17]=1[F:23].C(N(CC)CC)C.[Cl:31][C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[CH:48]=[C:47]([CH3:49])[O:46][N:45]=1>C(Cl)(Cl)Cl.O>[ClH:31].[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:32]([NH:43][C:44]2[CH:48]=[C:47]([CH3:49])[O:46][N:45]=2)=[O:34])=[CH:18][C:17]=1[F:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 661723-Amino-5-methylisoxazoleHCID 94429TriphosgeneHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Product 1

HCID 23118609HCID 23118609, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (800 mg) was dissolved in chloroform (20 ml) and triethylamine (1.0 ml) to prepare a solution. A solution of triphosgene (378 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, 3-amino-5-methylisoxazole (294 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Iced water was added to the reaction solution, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine and was then dried over anhydrous sodium sulfate. The dried organic layer was filtered and was then concentrated. Ether was added to the residue for crystallization, and the crystal was collected by filtration. The collected solid was purified by chromatography (chloroform:acetone=2:1). A 10% solution of hydrogen chloride in methanol was added to the purification product, followed by concentration. The resultant crystal was washed with ether to give 598 mg of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. filtrationThe dried organic layer was filtered
  6. concentrationwas then concentrated
  7. additionEther was added to the residue for crystallization
  8. filtrationthe crystal was collected by filtration
  9. customThe collected solid was purified by chromatography (chloroform:acetone=2:1)
  10. additionA 10% solution of hydrogen chloride in methanol was added to the purification product
  11. concentrationfollowed by concentration
  12. washThe resultant crystal was washed with ether

Sources & evidence

ORD record
ord-b11845f640174a54983e9923c02df52f
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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