Ethyl isocyanate → HCID 66777514, compound

HRID 2091216Notes

Reaction equation

HRID 2091216 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[CH:20][CH:19]=3)[CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:7]([CH3:35])[C:6]=2[CH:36]=1.C(N(CC)CC)C.[CH2:44]([N:46]=[C:47]=[O:48])[CH3:45]>O1CCCC1>[CH:11]1([CH:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[CH:20][CH:19]=2)[C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:47](=[O:48])[NH:46][CH2:44][CH3:45])=[CH:36][C:6]=3[C:7]=2[CH3:35])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471Triethylamine2×HCID 66778821HCID 66778821, compound

Product 1

HCID 66777514HCID 66777514, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mL) of ethyl 3-{[(4-{[(5-amino-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (280 mg) synthesized in Example A110(5) in tetrahydrofuran were added triethylamine (95 μL) and ethyl isocyanate (54 μL), and the mixture was stirred at room temperature for 1 day. Triethylamine (95 μL) and ethyl isocyanate (54 μL) were additionally added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (60-100% ethyl acetate/hexane) to give the title object compound (304 mg, 95%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (60-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0fb1cafb58cc4b2e85f61015511eec8b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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