Hydrochloric Acid → HCID 25267778, compound

HRID 1192858Notes

Reaction equation

HRID 1192858 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].[C:16]([C:18]1([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][C:33]#[N:34])=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1)#N.C[OH:36].Cl>CN(C=O)C.O>[C:33]([CH2:32][CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([N:23]2[C:18]3([CH2:22][CH2:21][CH2:20][CH2:19]3)[C:16](=[O:36])[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:2]2=[S:3])=[CH:25][CH:26]=1)#[N:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 57672608HCID 57672608, compound

Product 1

HCID 25267778HCID 25267778, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-Isothiocyanato-2-trifluoromethylbenzonitrile (96) (36 mg, 0.16 mmol) and 4-[4-(1-Cyanocyclopentyl amino)phenyl]butanenitrile (93) (20 mg, 0.08 mmol) in DMF (1 mL) was heated under microwave irradiation at 80° C. for 6 h. To this mixture was added methanol (10 mL) and aq. 1 N HCl (3 mL). The second mixture was refluxed for 1.5 h. After being cooled to room temperature, the reaction mixture was poured into cold water (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1) to give 4-(1-(4-(3-Cyanopropyl)phenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]non-3-yl)-2-trifluoromethylbenzonitrile (92) [ND-2]

Workup

  1. temperatureThe second mixture was refluxed for 1.5 h
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-749dc542c194422099cf359323e4119f
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

Loading…