p-Toluenesulfonic acid → HCID 57691009, compound

HRID 1511274Notes

Reaction equation

HRID 1511274 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 91 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 91 sodium carbonate and volatiles
  7. customremoved
  8. filtrationCollected product by filtration

Sources & evidence

ORD record
ord-570e6b085fc54651a8a3dbd0f7270eff
Source dataset
uspto-grants-2012_07
Patent number
US08212041B2

Reaction notes

Loading…