Ethyl isocyanate → HCID 118071542, compound

HRID 1775455Notes

Reaction equation

HRID 1775455 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17].O1CCCC1.C(N(CC)CC)C.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33]>CO>[CH2:32]([NH:34][C:35]([NH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17])=[O:36])[CH3:33]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 118071469HCID 118071469, compound

Product 1

HCID 118071542HCID 118071542, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-(2-aminoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide hydrochloride (100 mg) were added tetrahydrofuran (1.20 mL), triethylamine (0.147 mL), and ethylisocyanate (0.0415 mL), followed by stirring for 1 hour. To the mixture were added silica gel and methanol, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 94:6) to obtain a colorless solid. The obtained solid was washed with hexane/ethyl acetate to obtain 3-{2-[(ethylcarbamoyl)amino]ethyl}-5-methoxy-N-methyl-1H-indole-2-carboxamide (86.0 mg) as a colorless solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 94:6)
  3. customto obtain a colorless solid
  4. washThe obtained solid was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-51b7e7cdf5974c519e59a3e8fe88300c
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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