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Ethyl isocyanate → 1-ethyl-3-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-urea

HRID 448418
Notes
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Reaction equation

HRID 448418 reaction equation
N12CCCN=C1CCCCC2.Cl.[NH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:34])[N:18]([C:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24].[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>C(#N)C>[CH2:35]([NH:37][C:38]([NH:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:34])[N:18]([C:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24])=[O:39])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21988585HCID 21988585, compound

Product 1

HCID 583071391-ethyl-3-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-ureaYield 55%

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.2 g, 2.2 mmol) was added to a stirred suspension of 4-aminomethyl-2-(3-methyl-2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (0.3 g, 1.0 mmol) in acetonitrile (40 mL). After stirring for 30 minutes, ethyl isocyanate (0.09 g, 1.3 mmol) was added, and the mixture was stirred at room temperature for 24 hours. The mixture was concentrated and the residue was dissolved in methylene chloride (60 mL). The methylene chloride solution was washed with water (2×30 mL) and brine (30 mL), and dried (MgSO4). Solvent was removed and purified by chromatography (silica gel) to give 1-ethyl-3-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-urea (0.2 g, 55%) as a white solid: mp 220-222° C.; 1H NMR (DMSO-d6) δ 0.99 (t, J=7.1 Hz, 3H, CH3), 1.90 (s, 3H, CH3), 2.03-2.09 (m, 1H), 2.50-2.74 (m, 3H), 2.97-3.07 (m, 2H), 4.59 (d, J=5.8 Hz, 2H), 6.09 (t, J=5.0 Hz, 1H), 6.41 (t, J=5.6 Hz, 1H), 7.65-7.82 (e, 3H, Ar), 11.01 (s, 1H, NH); 13C NMR (DMSO-d6) δ 15.59, 21.01, 28.58, 29.11, 34.16, 38.65, 58.69, 121.25, 126.64, 131.37, 133.26, 134.46, 140.79, 157.92, 167.78, 168.41, 172.14, 172.22; Anal. calcd. for C18H20N4O5+0.08H2O: C, 57.83; H, 5.44; N, 14.99. Found: C, 57.26; H, 5.21; N, 14.79.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride (60 mL)
  4. washThe methylene chloride solution was washed with water (2×30 mL) and brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed
  7. custompurified by chromatography (silica gel)

Sources & evidence

ORD record
ord-2fab68e2924c4b43a14a95cc53b6d1eb
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481568B2

Reaction notes

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