Dimethylformamide → HCID 57387081, compound

HRID 1874518Notes

Reaction equation

HRID 1874518 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=2)C(O)=O)[N:10]=3)=[O:5])[CH2:3][CH2:2]1.C1(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.CN(C)C=O>O>[NH2:40][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][CH:23]=1)[O:16][C:11]1[N:10]=[C:9]2[S:8][C:7]([NH:6][C:4]([CH:1]3[CH2:2][CH2:3]3)=[O:5])=[N:15][C:14]2=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 57749236HCID 57749236, compound

Product 1

HCID 57387081HCID 57387081, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)benzoic acid (3.90 g, 11.0 mmol), diphenylphosphoryl azide (3.55 mL, 16.5 mmol), triethylamine (2.28 mL, 16.5 mmol) and N,N-dimethylformamide (80 mL) was stirred at room temperature for 3 hr, and water (20 mL) was added and the mixture was stirred at 100° C. for 15 hr. The precipitation solid was collected by filtration. 6N Hydrochloric acid (100 mL), ethyl acetate (30 mL) and tetrahydrofuran (10 mL) were added to the solid, and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off, and the aqueous layer was separated from the filtrate, neutralized with 8N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (1.13 g, 31%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 100° C. for 15 hr
  2. customThe precipitation solid
  3. filtrationwas collected by filtration
  4. addition6N Hydrochloric acid (100 mL), ethyl acetate (30 mL) and tetrahydrofuran (10 mL) were added to the solid
  5. stirringthe mixture was stirred at room temperature for 30 min
  6. filtrationThe insoluble material was filtered off
  7. customthe aqueous layer was separated from the filtrate
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltrated
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. filtrationthe residue was collected by filtration
  14. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-42f6dcb2bc254f4098960593eed4c64a
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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