Hydrochloric Acid → HCID 15952780, compound

HRID 244981Notes

Reaction equation

HRID 244981 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][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2([C:29]#N)[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1.C[OH:32].Cl>CN(C=O)C.O>[O:32]=[C:29]1[C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[N:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=2)[C:2](=[S:3])[N:1]1[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2430911-(4-Methylanilino)cyclopentane-1-carbonitrileHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Product 1

HCID 15952780HCID 15952780, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1a (0.296 g, 1.3 mmol) and 8a (0.2 g, 1 mmol) in dry DMF (0.2 ml) was stirred for 48 h. To this mixture were added methanol (10 ml) and HCl aq. 2N (3 ml). The second mixture was refluxed for 6 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 chromatographed (dichloromethane) to yield 4-(4-Oxo-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.4]non-3-yl)-2-trifluoromethylbenzonitrile, 8b, [RD35] (0.3 g, 0.7 mmol, 70%) as a white powder.

Workup

  1. temperatureThe second mixture was refluxed for 6 h
  2. extractionextracted with ethyl acetate (30 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane)

Sources & evidence

ORD record
ord-e063953a31424260a5b2046cf05c417b
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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