Potassium Iodide → HCID 11773954, compound

HRID 1435701Notes

Reaction equation

HRID 1435701 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[CH3:20])(=[O:12])=[O:11])[S:7][CH:8]=1.Br[CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26].CCN(C(C)C)C(C)C.[I-].[K+]>C(O)C.CS(C)=O>[Cl:19][C:15]1[C:14]([CH3:20])=[C:13]([S:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][N:1]3[CH2:22][CH2:23][CH2:24][C:25]3=[O:26])[N:5]=2)(=[O:11])=[O:12])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 76300Ethyl 4-bromobutyrateHCID 81531DiisopropylethylamineHCID 87546608HCID 87546608, compound

Product 1

HCID 11773954HCID 11773954, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A mixture of EXAMPLE 200A (200 mg, 0.60 mmol), ethyl 4-bromobutyrate (118 mg, 0.60 mmol), DIEA (156 mg, 1.20) and potassium iodide (10 mg, 0.06 mmol) in ethanol (5 mL)/DMSO (2 mL) was refluxed overnight, allowed to cool to room temperature, and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulphate, filtered and the solvent was evaporated. The residue was purified by flash chromatography on silica gel eluting with 20% acetone in DCM giving 18 mg (7%) of solid material: 1H NMR (CDCl3) δ 2.00 (qn, 2H), 2.38 (t, 2H), 2.65 (s, 3H), 2.88 (t, 2H), 3.40 (t, 2H), 3.58 (t, 2H), 6.24 (s, 1H), 7.22 (t, 1H), 7.52 (dd, 1H), 8.01 (dd, 1H); MS (Ionspray, [M+H]+) m/z 399.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20% acetone in DCM giving 18 mg (7%) of solid material

Sources & evidence

ORD record
ord-6ce925366834425fabf41b5ab7c7ed3a
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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