Triphenylphosphine → 7,8-bis(4-chlorophenyl)-2-((6-morpholinopyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224207

Reaction equation

HRID 2224207 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O:44]1[CH2:49][CH2:48][N:47]([C:50]2[N:55]=[CH:54][C:53]([CH2:56]O)=[CH:52][CH:51]=2)[CH2:46][CH2:45]1>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]([CH2:56][C:53]4[CH:54]=[N:55][C:50]([N:47]5[CH2:48][CH2:49][O:44][CH2:45][CH2:46]5)=[CH:51][CH:52]=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

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2776465[6-(Morpholin-4-yl)pyridin-3-yl]methanolHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 119899577,8-bis(4-chlorophenyl)-2-((6-morpholinopyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared using 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, Ph3P (110 mg, 0.42 mmol) and (6-morpholinopyridin-3-yl)methanol (29 mg, 0.14 mmol) in THF (1.0 mL) and by following the procedure described in Example 2. The title compound, 7,8-bis(4-chlorophenyl)-2-((6-morpholinopyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (20.5 mg, 11%) was obtained as yellow powder. MS M+H=533; 1H NMR (CDCl3) 8.26 δ (1H, d, J=5.0 Hz), 8.15 (1H, s), 7.65 (1H, d, J=5.0 Hz), 7.25-7.36 (6H, m), 7.09 (2H, d, J=10.0 Hz), 6.60 (1H, d, J=10.0 Hz), 5.10 (2H, s), 3.80 (4H, t, J=5.0 Hz), 3.50 (4H, t, J=5.0 Hz).

Workup

  1. customThe title compound was prepared
  2. customprepared

Sources & evidence

ORD record
ord-8af37b27555740eaa845e7e885c28aa3
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Linked notes

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