Ethyl isocyanate → HCID 71667943, compound

HRID 1507438Notes

Reaction equation

HRID 1507438 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1.[N:21]([CH2:24][CH3:25])=[C:22]=[O:23]>CN(C)C=O>[CH2:24]([NH:21][C:22]([N:16]1[CH2:17][CH2:18][CH:13]([C:8]2[O:9][C:10]3[C:5]([C:6](=[O:20])[C:7]=2[CH3:19])=[CH:4][CH:3]=[C:2]([OH:1])[C:11]=3[CH3:12])[CH2:14][CH2:15]1)=[O:23])[CH3:25]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 117701633HCID 117701633, compound

Product 1

HCID 71667943HCID 71667943, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-3,8-dimethyl-2-(piperidin-4-yl)-4H-chromen-4-one (68 mg, 0.25 mmol) obtained in Example 7-2 in dimethylformamide (2 mL), isocyanatoethane (19 μL, 0.25 mmol) was added dropwise under cooling with ice, and then the mixture was brought back to room temperature and stirred for 2 days. The reaction solution was concentrated, and then the obtained residue was purified by reverse-phase HPLC to obtain 52 mg of the title compound (yield: 59%).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought back to room temperature
  3. concentrationThe reaction solution was concentrated
  4. customthe obtained residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-f5124e5e535349b28ba88ea3c38fd97d
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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