Triethylamine → HCID 69071048, compound

HRID 1987813Notes

Reaction equation

HRID 1987813 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([OH:11])=[C:8]([C:12]([OH:14])=O)[C:7](=[O:15])[N:6]([CH3:16])[C:5]=2[S:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][NH:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33].S(Cl)(Cl)=O>ClCCl.C(Cl)(Cl)Cl>[F:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[N:25]([CH3:24])[C:12]([C:8]1[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[S:4][CH:3]=[C:2]([CH3:1])[C:10]=2[C:9]=1[OH:11])=[O:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 17945247HCID 17945247, compoundHCID 69073340HCID 69073340, compound

Product 1

HCID 69071048HCID 69071048, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 6,7-dihydro-3,7-dimethyl-4-hydroxy-6-oxo-thieno[2,3-b]pyridine-5-carboxylic acid (4.18. mmol, 1.0 g) in dichloromethane (10 ml), triethylamine (4 equiv., 16.7 mmol, 2.4 ml) and N-methyl-2,5-difluoroaniline (1.2 equiv., 5.0 mmol, 720 mg) were added. To the mixture stirred under nitrogen and cooled to 0° C., a solution of thionyl chloride (1.3 equiv., 5.4 mmol, 0.4 ml) in dichloromethane (5 ml) then was added during 30 min. The stirring was continued at 0° C. for 1 h and then at room temperature for another 20 min. The reaction mixture was diluted with chloroform and quickly washed with cold 1M sulphuric acid. The organic phase then was immediately extracted with 0.5 M NaOH. Remaining traces of chlorinated organic solvents were removed using a rotary evaporator. The pH was adjusted to just above the point where the desired product starts to precipitate (approximately pH 6.5) and the solution was filtered through celite. The product was precipitated by acidification with 1 M HCl until pH was approximately 1-2 and the mixture was allowed to stand for 2 hrs. The resulting precipitate was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (1.26 g, 83%).

Workup

  1. waitat room temperature for another 20 min
  2. washquickly washed with cold 1M sulphuric acid
  3. extractionThe organic phase then was immediately extracted with 0.5 M NaOH
  4. customRemaining traces of chlorinated organic solvents were removed
  5. customa rotary evaporator
  6. customto precipitate (approximately pH 6.5) and the solution
  7. filtrationwas filtered through celite
  8. customThe product was precipitated by acidification with 1 M HCl until pH was approximately 1-2
  9. waitto stand for 2 hrs
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with water
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-3d7419d59f3e41acbe3855e6fb6871b7
Source dataset
uspto-grants-2009_06
Patent number
US07553849B2

Reaction notes

Loading…