Hydrochloric Acid → HCID 15951525, compound

HRID 1927353Notes

Reaction equation

HRID 1927353 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[S:3].[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2([C:31]#N)[CH2:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18].C[OH:34].Cl>CN(C=O)C.O>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:2](=[S:3])[N:1]([C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=3)[C:31](=[O:34])[C:27]32[CH2:30][CH2:29][CH2:28]3)=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 67132096HCID 67132096, compound

Product 1

HCID 15951525HCID 15951525, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-isothiocyanato-2-trifluoromethylbenzonitrile (1a) (0.0.141 g, 0.62 mmol) and 1-(4-methanesulfonylphenylamino)cyclobutanecarbonitrile (45a) (0.11 g, 0.42 mmol) in dry DMF (2 ml) was stirred at room temperature for 3 days. To this mixture were added methanol (10 ml) and aq. 2N HCl (5 ml). The second mixture was refluxed for 3 h. After being cooled to room temperature, the reaction mixture was poured into cold water (10 ml) and extracted with ethyl acetate (3×30 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane:acetone, 97:3) to yield 4-[5-(4-methanesulfonylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-7-yl]-2-trifluoromethylbenzonitrile (45b) [RD145] (0.031 g, 0.065 mmol, 15%), the structure of which is illustrated in Formula 14, as a white powder.

Workup

  1. temperatureThe second mixture was refluxed for 3 h
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane:acetone, 97:3)

Sources & evidence

ORD record
ord-a753e32b5bc442fa9c67a45301c0ef37
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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