Potassium Iodide → HCID 178491853, compound

HRID 1371759Notes

Reaction equation

HRID 1371759 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:19])[C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=2[F:18])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([CH2:31][CH2:32][CH2:33]Cl)(=[O:30])=[O:29])[CH2:23][CH2:22]2)[N:3]=1.C([O-])(=[O:37])C.[K+].[I-].[K+]>C(O)C>[NH2:1][C:2]1[C:7]([C:8](=[O:19])[C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=2[F:18])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([CH2:31][CH2:32][CH2:33][OH:37])(=[O:30])=[O:29])[CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 178491850HCID 178491850, compound

Product 1

HCID 178491853HCID 178491853, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The chloride (80 mg, 0.18 mmol, Example 293) was dissolved in ethanol (1 mL). To it was added potassium acetate (86.5 mg, 0.88 mmol) and potassium iodide (8 mg, 0.05 mmol). The mixture was heated in a pressure tube in a microwave for 30 minutes. The mixture was filtered and the solid was washed with ethanol (4 mL). The filtrate (about 5 mL) was treated with 5% potassium hydroxide (2 mL) and the solution was stirred at room temperature for 30 minutes. The solution was neutralized with trifluoroacetic acid and concentrated. The residue was purified by reversed phase HPLC to give a pale yellow solid. 25 mg, 28%. MS (ES) MH+=500.

Workup

  1. temperatureThe mixture was heated in a pressure tube in a microwave for 30 minutes
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with ethanol (4 mL)
  4. additionThe filtrate (about 5 mL) was treated with 5% potassium hydroxide (2 mL)
  5. concentrationconcentrated
  6. customThe residue was purified by reversed phase HPLC
  7. customto give a pale yellow solid

Sources & evidence

ORD record
ord-85d8ff60401e474aae1f38fbc06f4467
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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