Acetonitrile → HCID 46937885, compound

HRID 2370345Notes

Reaction equation

HRID 2370345 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=3)[C:10]2=[S:29])=[CH:5][C:4]=1[F:30].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(O)(C(F)(F)F)=O.C(#N)C>C1(C)C=CC=CC=1>[F:30][C:4]1[CH:5]=[C:6]([N:9]2[C:13]([CH3:14])([CH3:15])[C:12](=[O:16])[N:11]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:27])([F:28])[F:26])[CH:18]=3)[C:10]2=[S:29])[CH:7]=[CH:8][C:3]=1[CH2:2][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 86668135HCID 86668135, compound

Product 1

HCID 46937885HCID 46937885, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 6 was prepared according to General Method 2. A solution of 4-(3-(4-(chloromethyl)-3-fluorophenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile (100 mg, 0.21 mmol) and pyrrolidine (78 mg, 1.05 mmol) in toluene (10 mL) was refluxed for 12 h. The solvent was removed and residue was purified by silica gel chromatography (eluant: 60% ethyl acetate in hexane) to obtain 13 mg of 4-(3-(3-fluoro-4-((pyrrolidin-1-yl)methyl)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-trifluoromethyl)benzonitrile, HPLC, Column: SUNFIRE C18, 4.6×250 mm, 5 μm, Mobile Phase A: 0.05% TFA, Mobile Phase B: ACN, Gradient: 10% to 90% B in 10 min, hold for 10 min. 90% to 10% B in 1 min, Flow Rate: 1 mL/min, Retention time: 7.491 min, M+1, 491.

Workup

  1. customThe solvent was removed
  2. customresidue was purified by silica gel chromatography (eluant: 60% ethyl acetate in hexane)
  3. customto obtain 13 mg of 4-(3-(3-fluoro-4-((pyrrolidin-1-yl)methyl)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-trifluoromethyl)benzonitrile, HPLC, Column
  4. wait90% to 10% B in 1 min

Sources & evidence

ORD record
ord-c74c9482f11b48909dd8b0b5462b405f
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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