Iodoacetamide → HCID 69291846, compound

HRID 1247431Notes

Reaction equation

HRID 1247431 reaction equation
[NH2:1][C:2]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:3]=1[CH2:4][C:5]([O:18][CH2:19][CH3:20])([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[F:17])[C:6]([NH2:8])=[O:7].I[CH2:28][C:29]([NH2:31])=[O:30].C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O.O>[C:29]([CH2:28][NH:1][C:2]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:3]=1[CH2:4][C:5]([O:18][CH2:19][CH3:20])([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[F:17])[C:6]([NH2:8])=[O:7])(=[O:30])[NH2:31]

Participants

7

Reactant 3

HCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 69290262HCID 69290262, compound

Product 1

HCID 69291846HCID 69291846, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of (RS)-(2-amino-4-cyano-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide (470 mg) in DMF (8 ml) were added iodoacetamide (376 mg) and N-ethyldiisopropylamine (0.34 ml). After 50 hrs stirring at 110° C. under argon atmosphere. The mixture was diluted with EtOAc and water. The organic phase was separated and washed with water and brine, dried ovef MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2=>CH2Cl2/MeOH 4:1) to give (RS)-[2-(carbamoylmethyl-amino)-4-cyano-benzyl]-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide (133 mg) as an off-white solid. MS 415.1([M+H]+)

Workup

  1. customThe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialdried ovef MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (CH2Cl2=>CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-4fdf8b17c23f40ccb9fcbcd3266f011f
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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