N-Methylcyclohexylamine → HCID 46937883, compound

HRID 2370343Notes

Reaction equation

HRID 2370343 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].[CH3:31][NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C1(C)C=CC=CC=1>[CH:33]1([N:32]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N:9]3[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=4)[C:10]3=[S:29])=[CH:5][C:4]=2[F:30])[CH3:31])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 86668135HCID 86668135, compound

Product 1

HCID 46937883HCID 46937883, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 4 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 (40 mg, 0.08 mmol) and N-methylcyclohexanamine (30 mg, 0.24 mmol) in toluene 5 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 7 mg of desired product as brown viscous oil, HPLC, Column: YMC ODS AQ, 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: 9.663 min, M+1, 533

Workup

  1. customCompound 4 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-69124777d8cc4cb19adb9cabf8118871
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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