Pyrrolidine → 5-(5-Fluoro-pyridin-2-ylmethoxy)-2-[2-(2-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-2-oxo-ethyl]-2H-pyridazin-3-one

HRID 1425770Notes

Reaction equation

HRID 1425770 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:27])[CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)[CH:13]=[N:12]2)=[C:5]([CH3:28])[CH:4]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:14]2[CH:13]=[N:12][N:11]([CH2:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:4][C:5]=3[CH3:28])=[O:27])[C:16](=[O:17])[CH:15]=2)=[N:21][CH:22]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 866955482-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-fluoro-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Product 1

HCID 717310465-(5-Fluoro-pyridin-2-ylmethoxy)-2-[2-(2-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-2-oxo-ethyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-fluoro-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 6b, 112 mg, 0.25 mmol) in DMF (2 mL) is added pyrrolidine (63 μL, 0.75 mmol). The reaction mixture is stirred for 60 min at room temperature. The mixture is purified via reverse phase HPLC chromatography (Gilson 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 (Gilson Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-35bc9c9a2e70425a95b800f1b2d0a1c5
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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