(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamide → (RS)-N-(4-cyano-2-methylcarbamoylmethoxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamide

HRID 1247358Notes

Reaction equation

HRID 1247358 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9](=[O:23])[CH:10]([C:13]2[C:18]([F:19])=[CH:17][C:16]([O:20][CH3:21])=[CH:15][C:14]=2[F:22])[O:11][CH3:12])=[C:5]([OH:26])[CH:4]=1)#[N:2].Cl[CH2:28][C:29]([NH:31][CH3:32])=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9](=[O:23])[CH:10]([C:13]2[C:14]([F:22])=[CH:15][C:16]([O:20][CH3:21])=[CH:17][C:18]=2[F:19])[O:11][CH3:12])=[C:5]([O:26][CH2:28][C:29](=[O:30])[NH:31][CH3:32])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 21905527(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamideHCID 865930472-chloro-N-methylacetamide cesium carbonate

Product 1

HCID 21905466(RS)-N-(4-cyano-2-methylcarbamoylmethoxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 16.4, (RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamide was alkylated with 2-chloro-N-methylacetamide/cesium carbonate in DMF to give (RS)-N-(4-cyano-2-methylcarbamoylmethoxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-acetamide as a colorless foam. MS 434.2 ([M+H]+)

Sources & evidence

ORD record
ord-0982cbe5c5fd4888ad5aaa14eecf991e
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…