4-((2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)-3-fluoroaniline → HCID 57967285, compound

HRID 1047434Notes

Reaction equation

HRID 1047434 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][C:23]=3[F:29])[CH:13]=2)=[N:10][CH:11]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]([CH3:44])[C:38](=[O:43])[CH2:39][C:40](O)=[O:41])=[CH:33][CH:32]=1>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[F:29][C:23]1[CH:24]=[C:25]([NH:26][C:40](=[O:41])[CH2:39][C:38]([N:37]([C:34]2[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=2)[CH3:44])=[O:43])[CH:27]=[CH:28][C:22]=1[O:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:3])=[CH:11][N:10]=3)[S:20][C:19]=12

Participants

6

Reactant 2

HCID 579195224-((2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)-3-fluoroanilineHCID 57967282HCID 57967282, compound

Product 1

HCID 57967285HCID 57967285, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To intermediate 38 (0.35 g, 0.86 mmol) in dry DMF (25 mL) was added 3-((4-fluorophenyl)(methyl)amino)-3-oxopropanoic acid (44) [U.S. 2007/0004675 A1] (0.36 g, 1.7 mmol) [Met-036], and EDCHCl (0.33 g, 1.7 mmol) and the mixture was stirred at r.t. for 2 h. The mixture was then partitioned between ethyl acetate and water; the organic phase was collected, washed with water, saturated NaHCO3, and brine, dried (anhydrous MgSO4), filtered and concentrated. The crude product was dissolved in acetone (50 mL) to give a colorless solution. The solution was diluted with water (20 mL) and TFA (2 mL), and heated to reflux for 3 h. It was then cooled and concentrated. The residue was then partitioned between ethyl acetate and water, the organic phase was collected, washed with water, saturated NaHCO3, and brine, dried (anhydrous MgSO4), filtered and concentrated to produce intermediate 45 (0.27 g, 57% yield). MS (m/z): 559.2 (M+H).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic phase was collected
  3. washwashed with water, saturated NaHCO3, and brine
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in acetone (50 mL)
  8. customto give a colorless solution
  9. temperatureheated
  10. temperatureto reflux for 3 h
  11. temperatureIt was then cooled
  12. concentrationconcentrated
  13. customThe residue was then partitioned between ethyl acetate and water
  14. customthe organic phase was collected
  15. washwashed with water, saturated NaHCO3, and brine
  16. dry with materialdried (anhydrous MgSO4)
  17. filtrationfiltered
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-81dd87e887124c359d857add88d3765c
Source dataset
uspto-grants-2013_10
Patent number
US08569503B2

Reaction notes

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