Triphenylphosphine → HCID 59716538, compound

HRID 2224217Notes

Reaction equation

HRID 2224217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[C:25]1([NH:31][CH2:32][CH2:33]O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH2:33][CH2:32][NH:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31235N-(2-Hydroxyethyl)anilineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716538HCID 59716538, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (2 ml) of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (50 mg, 0.14 mmol), prepared as described in Example 1, 2-(phenylamino)ethanol (19 mg, 0.13 mmol), triphenylphosphine (55 mg, 0.21 mmol) was added diethyl azodicarboxylate (0.09 ml, 42% wt in toluene, 0.21 mmol). After 1 h, the reaction mixture was concentrated. The crude material was purified by preparative HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(2-(phenylamino)ethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (14.4 mg, 23%) as a yellow solid. MS M+H=476; 1H NMR (CDCl3) δ 8.20 (1H), 7.41-7.20 (11H), 7.10 (2H), 4.51 (2H), 3.91 (2H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-c3bdc79a630e44d98eace78c5ea114cc
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

Loading…