Iodoacetamide → HCID 178468072, compound

HRID 1247406Notes

Reaction equation

HRID 1247406 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][NH:8][C:9](=[O:29])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])=[CH:16][C:15]=2[F:28])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].I[CH2:33][C:34]([NH2:36])=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[NH2:44][OH:45]>CN(C=O)C>[C:34]([CH2:33][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:17]1[CH:16]=[C:15]([F:28])[C:14]([CH:10]([O:11][CH2:12][CH3:13])[C:9]([NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1](=[NH:2])[NH:44][OH:45])=[CH:31][CH:30]=2)=[O:29])=[C:19]([F:20])[CH:18]=1)(=[O:35])[NH2:36]

Participants

6

Reactant 4

HCID 3727IodoacetamideHCID 10796Cesium carbonateHCID 443297Hydroxyamine hydrochlorideHCID 21905739HCID 21905739, compound

Product 1

HCID 178468072HCID 178468072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 16.4, (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-2′-hydroxy-biphenyl-4-yl)-2-ethoxy-acetamide (example 256.1) was alkylated with iodoacetamide and cesium carbonate in DMF. The product of this reaction was reacted with hydroxylamine hydrochloride in analogy to example 15.5 to give (RS)-2-(2′-carbamoylmethoxy-3,5-difluoro-biphenyl-4-yl)-2-ethoxy-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-acetamide. Colorless solid. MS 513.1 ([M+H]+)

Sources & evidence

ORD record
ord-d4285d0474544066ad976a82075b2dd4
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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