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

HRID 2224206Notes

Reaction equation

HRID 2224206 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.[CH2:44]([N:51]1[CH2:55][CH2:54][CH2:53][C@H:52]1[CH2:56]O)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[CH2:44]([N:51]1[CH2:55][CH2:54][CH2:53][C@@H:52]1[CH2:56][N:15]1[C:14](=[O:17])[N:11]2[N:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:10]2=[N:16]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 719760[(2S)-1-benzylpyrrolidin-2-yl]methanolHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 69196874(R)-2-((1-benzylpyrrolidin-2-yl)methyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 11%

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 (S)-1-benzyl-2-pyrrolidinemethanol (27 mg, 0.14 mmol) in THF (1.0 mL) and by following the procedure described in Example 2. The title compound, (R)-2-((1-benzylpyrrolidin-2-yl)methyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (8 mg, 11%) was obtained as yellow powder. MS M+H=530; 1H NMR (CDCl3) δ 8.14 (1H, s), 7.22-7.38 (11H, m), 7.10 (2H, d, J=10.0 Hz), 4.61-4.63 (1H, m), 3.50-3.56 (2H, q, J=13.2 Hz), 3.01 (1H, d, J=10.0 Hz), 2.85 (1H, d, J=10.0 Hz), 2.37-2.42 (1H, t, J=10.7 Hz), 1.99-2.02 (2H, m), 1.82-1.95 (1H, m), 1.70-1.80 (2H, m).

Workup

  1. customThe title compound was prepared
  2. customprepared

Sources & evidence

ORD record
ord-c8fc958247e84d60ba2c3883eae06ae9
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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