Triphenylphosphine → 6-Chloro-N-(3-methoxyphenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-amine

HRID 346499Notes

Reaction equation

HRID 346499 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=O)[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16]([NH:19][NH2:20])=[CH:17][CH:18]=1.BrC(Cl)(Cl)C(Br)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(N(CC)CC)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]2[N:15]([C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:20][N:19]=2)[N:14]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 878433-Methoxyphenyl isocyanateHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 230579556-Chloro-N-(3-methoxyphenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-methoxyphenyl isocyanate and 3-chloro-6-hydrazinopyridazine in acetonitrile was stirred at room temperature for 30 minutes, and 1,2-dibromo-1,1,2,2-tetrachloroethane was added and the mixture was stirred at room temperature for further 2 hours. This reaction solution was combined with triethylamine and triphenylphosphine with cooling in ice, and stirred at room temperature for 3 days. Then, the reaction solution was concentrated under reduced pressure, purified by a standard method to obtain 6-chloro-N-(3-methoxyphenyl)-1,2,4-triazolo[4,3-b]pyridazin-3-amine. Dat (F:276).

Workup

  1. temperaturewith cooling in ice
  2. stirringstirred at room temperature for 3 days
  3. concentrationThen, the reaction solution was concentrated under reduced pressure
  4. custompurified by a standard method

Sources & evidence

ORD record
ord-add47ddbb43b4301bde53dd880d624ad
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

Loading…