Cesium carbonate → (S)-5-(5-Chloro-pyridin-2-ylmethoxy)-2-{2-[4-(2-hydroxymethyl-pyrrolidin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-2H-pyridazin-3-one

HRID 1425771Notes

Reaction equation

HRID 1425771 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]([Cl:26])=[CH:22][N:21]=3)[CH:13]=[N:12]2)=[C:5]([CH3:28])[CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:35]1[CH2:41][CH2:40][CH2:39][C@H:36]1[CH2:37][OH:38]>CN(C)C(=O)C>[Cl: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:35]4[CH2:41][CH2:40][CH2:39][C@H:36]4[CH2:37][OH:38])=[CH:4][C:5]=3[CH3:28])=[O:27])[C:16](=[O:17])[CH:15]=2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 640091L-ProlinolHCID 866955502-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-chloro-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Product 1

HCID 71730532(S)-5-(5-Chloro-pyridin-2-ylmethoxy)-2-{2-[4-(2-hydroxymethyl-pyrrolidin-1-ylmethyl)-2-methyl-phenyl]-2-oxo-ethyl}-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-chloro-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 7b, 110 mg, 0.24 mmol) in N,N-dimethylacetamide (2 mL) is added Cs2CO3 (194 mg, 0.60 mmol) and L-prolinol (37 mg, 0.36 mmol). The reaction mixture is stirred for 2 days at room temperature. The mixture is purified via reverse phase HPLC chromatography (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 (Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-da384e96351c4f67a5526cfae9d830a1
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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