Iodoacetamide → HCID 22064661, compound

HRID 1828083Notes

Reaction equation

HRID 1828083 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][NH:8][C:9](=[O:27])[CH:10]([O:24][CH2:25][CH3:26])[N:11]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[OH:23])=[N:12]2)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:37][C:38]([NH2:40])=[O:39]>CN(C=O)C.CCOC(C)=O.O>[C:38]([CH2:37][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:13]1[C:14]([CH3:16])=[CH:15][N:11]([CH:10]([O:24][CH2:25][CH3:26])[C:9]([NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:29][CH:28]=2)=[O:27])[N:12]=1)(=[O:39])[NH2:40]

Participants

7

Reactant 3

HCID 3727IodoacetamideHCID 10796Cesium carbonateHCID 135724450HCID 135724450, compound

Product 1

HCID 22064661HCID 22064661, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(2-hydroxy-phenyl)-4-methyl-pyrazol-1-yl]-acetamide (200 mg) at r.t. in DMF (4 ml) under an argon atmosphere were added cesium carbonate (200 mg) followed by iodoacetamide (114 mg). The mixture was then stirred for 2 h. The mixture was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organics were washed with water. A solid started to precipitate out of the organic phase in the separating funnel. This solid was collected by filtration and washed with cyclohexane to give (RS)-2-[3-(2-carbamoylmethoxy-phenyl)-4-methyl-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (153 mg) as white powder. The organic layer of the filtrate was separated and washed with brine, dried (MgSO4), filtered and concentrated to leave a yellow solid. This was taken in Et2O (5 ml) and 5 drops of methanol were added. The suspension was stirred for 30 min at r.t. and this second crop of product was collected by filtration, washed with Et2O and dried to give more (RS)-2-[3-(2-carbamoylmethoxy-phenyl)-4-methyl-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (31 mg) of an off-white powder. MS 448.5 ([M+H]+)

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washThe combined organics were washed with water
  3. customto precipitate out of the organic phase in the separating funnel
  4. filtrationThis solid was collected by filtration
  5. washwashed with cyclohexane

Sources & evidence

ORD record
ord-8863df35be8f4873aba6f4f16ef759a4
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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