Triphenylphosphine → HCID 69197382, compound

HRID 2224205Notes

Reaction equation

HRID 2224205 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[CH2:45][C@@H:46]1[NH:50][C:49](=[O:51])[CH2:48][CH2:47]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]([CH2:45][C@H:46]4[CH2:47][CH2:48][C:49](=[O:51])[NH:50]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 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 69197382HCID 69197382, compoundYield 85%

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 (R)-5-(hydroxymethyl)pyrrolidin-2-one (17 mg, 0.14 mmol) in THF (1.0 mL) and by following the procedure described in Example 2. The title compound, (R)-7,8-bis(4-chlorophenyl)-2-((5-oxopyrrolidin-2-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (38.5 mg, 85%) was obtained as yellow powder. MS M+H=454; 1H NMR (CDCl3) δ 8.15 (1H, s), 7.24-7.36 (6H, m), 7.09 (2H, d, J=10.0 Hz), 6.59 (1H, s), 4.17-4.20 (1H, m), 4.03-4.10 (2H, m), 2.25-2.35 (3H, m), 1.92-2.02 (1H, m).

Workup

  1. customThe title compound was prepared
  2. customprepared

Sources & evidence

ORD record
ord-23ce8a2e0a7d4e68bb1ce2f16ecd81cf
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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