Iodoacetamide → HCID 25270556, compound

HRID 1516404Notes

Reaction equation

HRID 1516404 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[NH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.[H-].[Na+].I[CH2:34][C:35]([NH2:37])=[O:36]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[N:29][CH2:34][C:35](=[O:36])[NH2:37])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 25267402HCID 25267402, compound

Product 1

HCID 25270556HCID 25270556, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
42.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl sulfoximide (500 mg, 0.00108 mol) in DMF(2.5 mL) was added Sodium hydride (170 mg, 0.0036mol) at 25-30° C. under nitrogen atmosphere. Reaction mixture was stirred at 40-45° C. for 3 hr. Reaction mixture was cooled to 0-5° C. and to this was added iodoacetamide (240 mg, 0.0013 mol) and stirred for 12 hr at 25-30° C. Subsequent work up and column purification (100-200 mesh silica gel, 2% methanol in chloroform) gave 90 mg of titled product in 16% yield.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas cooled to 0-5° C.
  4. stirringstirred for 12 hr at 25-30° C
  5. customSubsequent work up and column purification (100-200 mesh silica gel, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-7de5976d475f434d9ebfbcb53f2eb173
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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