Potassium Iodide → HCID 178491843, compound

HRID 1371760Notes

Reaction equation

HRID 1371760 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.CC(C)([O-])C.[K+].[I-].[K+]>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=2[F:18])=[O:19])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([N:27]3[CH2:33][CH2:32][CH2:31][S:28]3(=[O:30])=[O:29])[CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 23665647Potassium tert-butoxideHCID 178491850HCID 178491850, compound

Product 1

HCID 178491843HCID 178491843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The chloride (530 mg, 1.02 mmol, Example 293) was dissolved in tetrahydrofuran (8 mL). To it was added potassium t-butoxide (395 mg, 3.53 mmol, Aldrich) and potassium iodide (10 mg). The mixture was heated at reflux for 3 hours and the reaction was quenched with 0.5N hydrochloric acid (1 mL). The mixture was extracted with ethyl acetate (3×10 mL) and the extracts were combined and dried with sodium sulfate. Removal of solvent gave the crude which was chromatographed (5% methanol/dichloromethane) to give a pale yellow solid. 412 mg, 85%. MS (ES) MH+=482. CDK4 IC50=0.005 μM; CDK1 IC50=0.028 μM; CDK2 IC50=0.008 μM; HCT 116 IC90=0.320 μM.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe reaction was quenched with 0.5N hydrochloric acid (1 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  5. dry with materialdried with sodium sulfate
  6. customRemoval of solvent
  7. customgave the crude which
  8. customwas chromatographed (5% methanol/dichloromethane)
  9. customto give a pale yellow solid

Sources & evidence

ORD record
ord-e7a266ed82bd4b49a2b68ecbcab3bf0d
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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