Potassium Iodide → HCID 58808668, compound

HRID 1921477Notes

Reaction equation

HRID 1921477 reaction equation
[I-].[K+].C[Si](C)(C)Cl.[CH2:8]([C:10]1[CH:11]=[C:12]([C:19]2[O:23][C:22]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)=[O:25])=[CH:21][CH:20]=2)[C:13]([CH3:18])=[N:14][C:15]=1[O:16]C)[CH3:9]>C(#N)C.O>[CH2:8]([C:10]1[C:15](=[O:16])[NH:14][C:13]([CH3:18])=[C:12]([C:19]2[O:23][C:22]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:28][CH2:27]3)=[O:25])=[CH:21][CH:20]=2)[CH:11]=1)[CH3:9]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 58808615HCID 58808615, compound

Product 1

HCID 58808668HCID 58808668, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Two equivalents of potassium iodide and two equivalents of trimethylchlorosilane are added to a solution of one equivalent of [5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)-furan-2-yl]-(4-phenylpiperazin-1-yl)-methanone in anhydrous acetonitrile (3-5 ml/mmol) under argon, the latter being prepared in accordance with the procedure set out in PREPARATION 6, and the cloudy mixture is heated at 60-80° C. for 1-3 h. The mixture is then cooled to rt and diluted with water. The precipitated product is filtered off with suction, washed with water and dried in a vacuum oven at 40° C. The filtrate is extracted with ethyl acetate and, after concentration, occasionally affords further product, which is purified by chromatography on silica gel. MS: m/e=392 (M+H). 1H NMR (D6-DMSO, δ ppm): 11.79 (s, 1H); 7.53 (s, 1H); 7.27 (m, 2H); 7.13 (d, 1H); 6.99 (m, 2H); 6.85 (m, 1H); 6.69 (d, 1H); 3.85 (br s, 4H); 3.23 (m, 4H); 2.50 (m, 5H); 1.12 (t, 3H).

Workup

  1. customthe latter being prepared in accordance with the procedure
  2. customset out in PREPARATION 6
  3. temperatureThe mixture is then cooled to rt
  4. filtrationThe precipitated product is filtered off with suction
  5. washwashed with water
  6. customdried in a vacuum oven at 40° C
  7. extractionThe filtrate is extracted with ethyl acetate
  8. concentrationafter concentration, occasionally affords further product, which
  9. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-34f26bc153864faa90b77a42b6df945a
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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