Iodine → HCID 68743737, compound

HRID 2095991Notes

Reaction equation

HRID 2095991 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[N:17]3)[CH2:10][CH2:9]2)[S:6][CH:7]=1)=O.CC1N(CC(N2CCC(C3SC=C(C4C=C(C5C=CC=CC=5)ON=4)N=3)CC2)=O)N=C(C(F)(F)F)C=1.[CH3:62][NH:63][CH:64]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[CH2:65][NH2:66].C(=O)([O-])[O-].[K+].[K+].II>C(O)(C)(C)C>[CH3:62][N:63]1[CH:64]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH2:65][N:66]=[C:1]1[C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[N:17]3)[CH2:10][CH2:9]2)[S:6][CH:7]=1

Participants

7

Reactant 5

HCID 807IodineHCID 11430Potassium CarbonateHCID 98060N1-Methyl-1-phenylethylenediamineHCID 687422261-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-[4-(5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidineHCID 86631244HCID 86631244, compound

Product 1

HCID 68743737HCID 68743737, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-(4-formyl-2-thiazolyl)-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine (i.e. the product of Example 2, Step B) (0.8 g, 2.07 mmol) in tert-butanol (5 mL) was added N1-methyl-1-phenyl-1,2-ethanediamine (43.57 mg, 0.29 mmol). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 30 minutes, and then potassium carbonate (107.8 mg, 0.78 mmol) and iodine (43.57 mg, 0.33 mmol) were added. The reaction mixture was stirred at 70° C. for 3 h and then quenched by addition of saturated aqueous sodium sulfite solution until the iodine color almost disappeared. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by preparative thin-layer chromatography on silica gel using a mixture of 94% ethyl acetate, 5% methanol and 1% triethylamine as eluant to give 64 mg of the title product as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 3 h
  2. customquenched by addition of saturated aqueous sodium sulfite solution until the iodine color
  3. extractionThe reaction mixture was extracted with chloroform
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin-layer chromatography on silica gel using
  9. additiona mixture of 94% ethyl acetate, 5% methanol and 1% triethylamine as eluant

Sources & evidence

ORD record
ord-fef34ff316314e6abcb093c4f2f4705b
Source dataset
uspto-grants-2013_05
Patent number
US08449898B2

Reaction notes

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