Phosphorus oxychloride → HCID 86639822, compound

HRID 1925157Notes

Reaction equation

HRID 1925157 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][CH2:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[CH:4][CH:3]=1.[Br:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][NH:27][C:28](=O)[CH:29]([C:31]2[N:32]=[N:33][C:34](Cl)=[CH:35][CH:36]=2)[CH3:30])=[N:24][CH:25]=1.P(Cl)(Cl)(Cl)=[O:40]>>[Br:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:28]([CH:29]([C:31]3[CH:36]=[CH:35][C:34]4[N:33]([CH:9]=[C:10]([NH:14][C:15]([CH:16]5[CH2:17][CH2:18]5)=[O:40])[N:11]=4)[N:32]=3)[CH3:30])=[N:27][N:26]=2)[CH:25]=1.[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][CH2:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 59233248HCID 59233248, compoundHCID 86639822HCID 86639822, compound

Product 2

HCID 59233190HCID 59233190, compoundHCID 86639822HCID 86639822, compoundYield 26.7%

Procedure

6-Bromo-3-((-(6-chloropyridazin-3-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridine (48D): A solution of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)propanehydrazide (13 g, 36.5 mmol) in phosphoryl trichloride (84 ml, 901 mmol) was heated in the microwave at 140° C. for 15 min. The reaction was concentrated via rotary evaporation and the resulting mixture was added drop-wise to a mixture of EtOAc:Saturated Bicarbonate (aq) (4:6, 1 L). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×75 mL). The EtOAc solutions were combined and evaporated to dryness. The resulting residue was purified by MPLC (DCM:MeOH, 97:3) to provide the title compound, 6-Bromo-3-(1-(6-chloropyridazin-3-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridine (48D, 3.3 g, 26.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.86 (d, J=7.07 Hz, 3 H) 5.27 (d, J=7.33 Hz, 1 H) 7.49 (dd, J=9.60, 1.77 Hz, 1H) 7.78 (dd, J=9.85, 1.01 Hz, 1 H) 7.94 (s, 2 H) 8.79 (s, 1 H). ESI-MS:m/z 339.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated via rotary evaporation
  2. additionthe resulting mixture was added drop-wise
  3. additionto a mixture of EtOAc
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×75 mL)
  6. customevaporated to dryness
  7. customThe resulting residue was purified by MPLC (DCM:MeOH, 97:3)

Sources & evidence

ORD record
ord-49571c5a9cb345df8e3e522ebceeb6c5
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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