4-Benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one → 2-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

HRID 1425755Notes

Reaction equation

HRID 1425755 reaction equation
C(OC1C=CN(CC(C2C=CC(C[Br:25])=CC=2C)=O)C(=O)C=1)C1C=CC=CC=1.O[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:55])[CH2:37][N:38]2[C:43](=[O:44])[CH:42]=[C:41]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][N:48]=3)[CH:40]=[N:39]2)=[C:32]([CH3:56])[CH:31]=1.C(OC1C=CN(CC(C2C=CC(CO)=CC=2C)=O)C(=O)C=1)C1C=CC=CC=1>COC(C)(C)C>[Br:25][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:55])[CH2:37][N:38]2[C:43](=[O:44])[CH:42]=[C:41]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][N:48]=3)[CH:40]=[N:39]2)=[C:32]([CH3:56])[CH:31]=1

Participants

5

Reactant 3

HCID 866955374-Benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-oneHCID 866955384-Benzyloxy-1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-oneHCID 866955552-[2-(4-Hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Product 1

HCID 866955562-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-oneYield 97%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

2-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one is prepared following preparation 1d employing 2-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 9c) instead of preparation 1c. The reaction mixture is stirred overnight. Tert-butyl methyl ether is added and the resulting precipitate is filtered off and dried.

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. customdried

Sources & evidence

ORD record
ord-b91d53c74f0644e8bd0f77c783eacb65
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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