HCID 86690140, compound → HCID 86690141, compound

HRID 1184349Notes

Reaction equation

HRID 1184349 reaction equation
[CH2:1]([NH:4][C:5]([NH:7][C:8]1[C:23]([F:24])=[CH:22][C:11]2[O:12][C:13]([F:21])([F:20])[C:14](=[O:19])[N:15]([CH2:16][C:17]#[CH:18])[C:10]=2[CH:9]=1)=[S:6])[CH2:2][CH3:3]>ClCCl>[CH2:1]([N:4]1[C:13](=[O:12])[C:14](=[O:19])[N:7]([C:8]2[C:23]([F:24])=[CH:22][C:11]3[O:12][C:13]([F:21])([F:20])[C:14](=[O:19])[N:15]([CH2:16][C:17]#[CH:18])[C:10]=3[CH:9]=2)[C:5]1=[S:6])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 86690140HCID 86690140, compound

Product 1

HCID 86690141HCID 86690141, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl oxalyl chloride (0.487 ml, 4.36 mmol) was added to a stirred solution of 1-propyl-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)thiourea (1197 mg, 3.35 mmol) in dichloromethane (20 ml) at room temperature under nitrogen. The resulting mixture was stirred overnight at room temperature, and then evaporated in vacuo. Toluene was added to the yellow residue, and the resulting suspension was refluxed for 3 hours, resulting in a clear solution. The reaction mixture was cooled to room temperature, and the resulting precipitate was isolated and washed with heptane to yield 792 mg of crude product. This was then recrystallised from toluene. Some remaining impurity was removed by dissolving the solid in ethyl aceate, washing with aqueous sodium bicarbonate solution, drying over sodium sulfate, and evaporating in vacuo to yield 667 mg of the title compound (purity>95%).

Workup

  1. customevaporated in vacuo
  2. additionToluene was added to the yellow residue
  3. temperaturethe resulting suspension was refluxed for 3 hours
  4. customresulting in a clear solution
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customthe resulting precipitate was isolated
  7. washwashed with heptane
  8. customto yield 792 mg of crude product
  9. customThis was then recrystallised from toluene
  10. customSome remaining impurity was removed
  11. dissolutionby dissolving the solid in ethyl aceate
  12. washwashing with aqueous sodium bicarbonate solution
  13. dry with materialdrying over sodium sulfate
  14. customevaporating in vacuo

Sources & evidence

ORD record
ord-a12e9a81ee0946958cb291945e00349b
Source dataset
uspto-grants-2014_03
Patent number
US08669208B2

Reaction notes

Loading…