Water → 4-([1,2,4]Triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzenamine

HRID 240588Notes

Reaction equation

HRID 240588 reaction equation
[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:19]=[CH:18][C:14](C(O)=O)=[C:13]([F:20])[C:12]=3[Cl:21])=[CH:6][C:5]=12.C([N:24](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.O>CN(C=O)C>[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:19]=[CH:18][C:14]([NH2:24])=[C:13]([F:20])[C:12]=3[Cl:21])=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 669372644-([1,2,4]Triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoic acid

Product 1

HCID 669370284-([1,2,4]Triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A vial was charged with 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoic acid (0.090 g, 0.2925 mmol), triethylamine (0.1223 ml, 0.8776 mmol) and DMF (1.5 ml). Diphenylphosphoryl azide (0.1630 ml, 0.7313 mmol) was added. The reaction was stirred at ambient temperature for 3 hours, then water (0.2199 ml, 0.2925 mmol) was added. The vial was sealed and heated to 100° C. for 1 hour, then cooled to ambient temperature and poured into 1 N NaOH/ice. The reaction was extracted with EtOAc, and the organic layer was dried, filtered and concentrated. The residue was purified by flash chromatography, eluting with a gradient from 100% EtOAc to 10% (with 6% NH4OH) MeOH/EtOAc.

Workup

  1. customThe vial was sealed
  2. temperatureheated to 100° C. for 1 hour
  3. temperaturecooled to ambient temperature
  4. extractionThe reaction was extracted with EtOAc
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with a gradient from 100% EtOAc to 10% (with 6% NH4OH) MeOH/EtOAc

Sources & evidence

ORD record
ord-635652f12a604e42a88650e67312f2fc
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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