Triethylamine → HCID 23118582, compound

HRID 1348836Notes

Reaction equation

HRID 1348836 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.C(N(CC)CC)C.[Cl:31]C(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[S:45][CH:46]=[C:47]([CH3:49])[N:48]=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:35]([NH:43][C:44]2[S:45][CH:46]=[C:47]([CH3:49])[N:48]=2)=[O:41])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 741432-Amino-4-methylthiazoleHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 23118582HCID 23118582, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (10 g) was dissolved in chloroform (300 ml) and triethylamine (40 ml) to prepare a solution. A solution of triphosgene (10 g) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 30 min. Next, 2-amino-4-methylthiazole (4.36 g) 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 magnesium sulfate. The dried organic layer was filtered and was then concentrated, and ether was added to the residue for crystallization, followed by collection of the resultant crystal by filtration. The crystal 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 6.0 g 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 magnesium sulfate
  5. filtrationThe dried organic layer was filtered
  6. concentrationwas then concentrated
  7. additionether was added to the residue for crystallization
  8. customfollowed by collection of the resultant crystal
  9. filtrationby filtration
  10. customThe crystal was purified by chromatography (chloroform:acetone=2:1)
  11. additionA 10% solution of hydrogen chloride in methanol was added to the purification product
  12. concentrationfollowed by concentration
  13. washThe resultant crystal was washed with ether

Sources & evidence

ORD record
ord-c3b3d580dd144289ab1a702ca8f741c7
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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