Triethylamine → HCID 22637142, compound

HRID 2416029Notes

Reaction equation

HRID 2416029 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][C:46]([CH3:49])=[CH:47][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][C:46]([CH3:49])=[CH:47][N:48]=2)=[O:41])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 3517702-Amino-5-methylthiazoleHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22637142HCID 22637142, compoundYield 161.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (300 mg) was dissolved in chloroform (6 ml) and triethylamine (0.3 ml) to prepare a solution. A solution of triphosgene (142 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, 2-amino-5-methylthiazole (119 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 crystal was purified by chromatography (chloroform:acetone=2:1). A 10% hydrogen chloride-methanol solution was added to the purified crystal, and the solution was then concentrated. The resultant crystal was washed with ether to give 380 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 crystal was purified by chromatography (chloroform:acetone=2:1)
  10. additionA 10% hydrogen chloride-methanol solution was added to the purified crystal
  11. concentrationthe solution was then concentrated
  12. washThe resultant crystal was washed with ether

Sources & evidence

ORD record
ord-a6a98fa0812d48cf884cb140e1cb8b67
Source dataset
uspto-grants-2004_11
Patent number
US06821987B2

Reaction notes

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