Triphenylphosphine → N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

HRID 406424Notes

Reaction equation

HRID 406424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]2[N:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N([Si](C)(C)C)=[N+]=[N-].N(C(OCC)=O)=NC(OCC)=O>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:18]3[N:17]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=4)[CH:15]=[CH:14][C:13]3=[N:12][N:11]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66849890N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide

Product 1

HCID 66849693N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask was added N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide (0.928 mmole), triphenylphosphine (3.25 mmole), azidotrimethylsilane (3.25 mmole), diethyl azodicarboxylate (4.18 mmole), and THF (13 mL). The resulting mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with dichloromethane and washed with saturated NaHCO3 and brine. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was washed with dichloromethane and methanol. The yellow solid was further purified by recrystallization with DMF and water to yield N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated in vacuo
  5. washThe crude product was washed with dichloromethane and methanol
  6. customThe yellow solid was further purified by recrystallization with DMF and water

Sources & evidence

ORD record
ord-2fced20407514264a633032760252a01
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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