Water → HCID 23114284, compound

HRID 2376493Notes

Reaction equation

HRID 2376493 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:28])[NH:6][C:7]1[C:8]([CH3:27])=[C:9]([CH3:26])[C:10]2[O:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[C:11]=2[C:24]=1[CH3:25].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH:21]([C:18]1[CH:17]=[CH:16][C:15]([CH:12]2[C:11]3[C:24]([CH3:25])=[C:7]([NH:6][C:5]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:28])[C:8]([CH3:27])=[C:9]([CH3:26])[C:10]=3[O:14][CH2:13]2)=[CH:20][CH:19]=1)([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 86618058HCID 86618058, compound

Product 1

HCID 23114284HCID 23114284, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,2,2-trichloroethyl(3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate (353 mg, 0.75 mmol) obtained in Example 138 and pyrrolidine (0.076 mL, 0.9 mmol) in dimethylsulfoxide (5 mL) was added diisopropylethylamine (0.13 mL, 0.75 mmol) at room temperature, and the resulting mixture was heated at 50° C. and reacted for 16 hours. The reaction solution was cooled to room temperature and poured into water, and the product was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 130 mg (yield: 44%) of the title compound. Melting point: 186-188° C.

Workup

  1. customreacted for 16 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-917e02abd4e44faca2c5b88dc4166485
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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