p-Toluenesulfonic acid → HCID 57691009, compound

HRID 219074Notes

Reaction equation

HRID 219074 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][C:19]=4[NH2:24])=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:25](OCC)(OCC)OCC.CC1C=CC(S(O)(=O)=O)=CC=1>>[N:17]1([CH2:16][C:13]2[N:11]3[N:12]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=[CH:9][C:10]3=[N:15][N:14]=2)[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N:24]=[CH:25]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 67503473N4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)pyridine-3,4-diamine

Product 1

HCID 57691009HCID 57691009, compound

Conditions

Temperature
60 °C

Procedure

A mixture of N4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)pyridine-3,4-diamine (0.0650 g, 0.20 mmol), triethyl orthoformate (5.0 ml, 30 mmol), and p-TsOH (0.0039 g, 0.020 mmol) was heated at 60° C. After 2 h reaction is complete. Reaction was concentrated. Took up in DMSO and purified on RPHPLC. Fractions containing product were treated with 9% sodium carbonate and volatiles removed. Collected product by filtration. MS m/z=328.1 [M+1]+. Calc'd for C18H13N7: 327.3.

Workup

  1. customAfter 2 h reaction
  2. customReaction
  3. concentrationwas concentrated
  4. custompurified on RPHPLC
  5. additionFractions containing product
  6. additionwere treated with 9% sodium carbonate and volatiles
  7. customremoved
  8. filtrationCollected product by filtration

Sources & evidence

ORD record
ord-1637a4b5160445b68439f808ae3c97eb
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

Loading…