Water → HCID 68441506, compound

HRID 1162447Notes

Reaction equation

HRID 1162447 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[N:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[NH:6][CH:7]=1.CCN(C(C)C)C(C)C.I[CH2:29][C:30]([NH2:32])=[O:31].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:6]([CH2:29][C:30]([NH2:32])=[O:31])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 178427411HCID 178427411, compound

Product 1

HCID 68441506HCID 68441506, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-(5-bromopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (step 1) (11.3 g, 34.5 mmol) in DMF (70 mL) was added Huenig's base (N-ethyldiisopropyl amine) (6.62 mL, 38.0 mmol) and 2-iodoacetamide (7.03 g, 38.0 mmol). The mixture was stirred at room temperature for 15 h. The mixture was poured into 750 mL of water. The mixture was stirred for 90 min and the solid precipitate was collected by filtration. The filter-cake was washed with water and then ether, and then dried at 70° C. under vacuum for 1 h to afford 2-(5-bromo-2-(4-methylphenylsulfonamido)pyridin-1(2H)-yl)acetamide (13.0 g, 98.0% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.37 (d, J=2.2 Hz, 1H), 7.88 (dd, J=9.7 Hz, 2.5 Hz, 1H), 7.79 (s, 1H), 7.65 (d, J=8.2 Hz, 2H), 7.39 (s, 1H), 7.29 (t, J=9.3 Hz, 3H), 4.79 (s, 2H), 2.34 (s, 3H).

Workup

  1. stirringThe mixture was stirred for 90 min
  2. filtrationthe solid precipitate was collected by filtration
  3. washThe filter-cake was washed with water
  4. dry with materialether, and then dried at 70° C. under vacuum for 1 h

Sources & evidence

ORD record
ord-52fac6aba27843489af9da009ebff03e
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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