Sodium Iodide → HCID 11548910, compound

HRID 2267464Notes

Reaction equation

HRID 2267464 reaction equation
[Br:1][C:2]1[C:3]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31]Cl)=[CH:28][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[C:3]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31][N:37]4[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]4)=[CH:28][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 60204658HCID 60204658, compound

Product 1

HCID 11548910HCID 11548910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1-(2-{5-Bromo-4-[5-(2-chloroethoxy)benzo[b]thiophen-2-yl]pyrimidin-2-ylamino}ethyl)-5,5-dimethylimidazolidine-2,4-dione (0.15 g, 0.27 mmol) was dissolved in DMF (2 mL) and treated with N-methylpiperazine (0.061 mL, 0.55 mmol) and catalytic amount of sodium iodide (0.025 g). The mixture was heated to 70° C. and stirred overnight. The reaction was cooled down to room temperature and poured into a saturated aqueous solution of sodium bicarbonate (15 mL). The resulting precipitate was collected by filtration, dissolved in DMF (2 mL) and purified by preparative HPLC. The clean fractions were treated with 2 M ammonia in methanol and the organic volatiles removed to give a suspension of a white solid in the aqueous layer, which was collected by filtration, washed well with water and dried overnight in a vacuum oven at 60° C. Yield=0.062 g. MS (M+H)+ 603/605.

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutiondissolved in DMF (2 mL)
  4. custompurified by preparative HPLC
  5. additionThe clean fractions were treated with 2 M ammonia in methanol
  6. customthe organic volatiles removed
  7. customto give
  8. additiona suspension of a white solid in the aqueous layer, which
  9. filtrationwas collected by filtration
  10. washwashed well with water
  11. customdried overnight in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-5981147d4cbe4056b8fb948666cdcd1b
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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