N-Methyl dicyclohexylamine → HCID 90224866, compound

HRID 1487091Notes

Reaction equation

HRID 1487091 reaction equation
[CH:1]([S:3]([N:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].Br[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([N:24]2[C:28]([CH3:30])([CH3:29])[C:27](=[O:31])[NH:26][C:25]2=[O:32])=[CH:19][C:18]=1[CH3:33].F[B-](F)(F)F.[H+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CN(C1CCCCC1)C1CCCCC1>CN1CCCC1=O>[O:13]1[C:9]2([CH2:8][CH2:7][N:6]([S:3](/[CH:1]=[CH:2]/[C:17]3[C:18]([CH3:33])=[CH:19][C:20]([N:24]4[C:28]([CH3:30])([CH3:29])[C:27](=[O:31])[NH:26][C:25]4=[O:32])=[CH:21][C:22]=3[CH3:23])(=[O:4])=[O:5])[CH2:15][CH2:14]2)[O:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 24210N-Methyl dicyclohexylamineHCID 66818416HCID 66818416, compoundHCID 90224863HCID 90224863, compoundHCID 118705180Tris(tert-butyl)phosphonium tetrafluoroborate

Product 1

HCID 90224866HCID 90224866, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 8-(vinylsulfonyl)-1,4-dioxa-8-azaspiro[4.5]decane (431 mg, 1.85 mmol), 1-(4-bromo-3,5-dimethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (575 mg, 1.85 mmol), tris(dibenzylidineacetone)palladium(0) (508 mg, 0.55 mmol), tri-tert-butylphosphine tetrafluoroboric acid (165 mg, 0.55 mmol), and methyldicyclohexylamine (2.1 mL, 9.25 mmol) in N-methyl-2-pyrrolidone (18.5 mL) was stirred under nitrogen atmosphere at 110° C. for two hours. The reaction mixture was cooled, quenched with water, and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by amino-silica gel column chromatography (dichloromethane-methanol) to afford (E)-1-(4-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylsulfonyl)vinyl)-3,5-dimethylphenyl)-5,5-dimeth ylimidazolidine-2,4-dione (584 mg, 68%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by amino-silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-8dea8a291484431f832680851dc41521
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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