Diethylamine → HCID 46937884, compound

HRID 2370344Notes

Reaction equation

HRID 2370344 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].[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32]>C1(C)C=CC=CC=1>[CH2:31]([N:33]([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])[CH2:34][CH3:35])[CH3:32]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86668135HCID 86668135, compound

Product 1

HCID 46937884HCID 46937884, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 5 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 diethyl amine (48 mg, 0.63 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 32 mg of 4-(3-(4-((diethylamino)methyl)-3-fluorophenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile as brown viscus oil, 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: 7.43 min, M+1, 493.

Workup

  1. customCompound 5 was prepared
  2. customThe solvent was removed
  3. customresidue was purified by silica gel chromatography (eluant: 60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c221a8451c9941339b26376e30be8c37
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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