Diisopropylethylamine → (R)-5-Benzyloxy-2-{2-[4-(3-hydroxy-piperidin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-2H-pyridazin-3-one

HRID 1425769Notes

Reaction equation

HRID 1425769 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[N:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH:29][C@@H:30]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[N:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:32]3[CH2:33][CH2:34][CH2:35][C@@H:30]([OH:29])[CH2:31]3)=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 866955465-Benzyloxy-2-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-2H-pyridazin-3-one

Product 1

HCID 86695568(R)-5-Benzyloxy-2-{2-[4-(3-hydroxy-piperidin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzyloxy-2-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-2H-pyridazin-3-one (preparation 5b, 100 mg, 0.23 mmol) in DMF (2 mL) is added (R)-3-hydroxypiperidine hydrochloride (96 mg, 0.70 mmol) and N-ethyldiisopropylamine (362 μL, 2.1 mmol). The reaction mixture is stirred overnight at room temperature. The mixture is purified via reverse phase HPLC chromatography (Waters Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min).

Workup

  1. customThe mixture is purified via reverse phase HPLC chromatography (Waters Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-8c87da2d0172448b8c0e7893aa55ef4a
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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