Triethylamine → HCID 58827298, compound

HRID 448431Notes

Reaction equation

HRID 448431 reaction equation
[C:1]1([CH3:10])[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.Cl.[NH2:12][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=[O:32])[N:17]([CH:24]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31])[C:18]2=[O:23].C(N(CC)CC)C>C1COCC1>[O:31]=[C:25]1[CH:24]([N:17]2[C:16](=[O:32])[C:15]3[C:19](=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13][NH:12][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:10])=[O:9])[C:18]2=[O:23])[CH2:29][CH2:28][C:27](=[O:30])[NH:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 219885254-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 1

HCID 58827298HCID 58827298, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

o-Tolyl isocyanate (0.4 g, 3.0 mmol) was added to a stirred suspension of 4-aminomethyl-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (0.8 g, 2.3 mmol) and triethylamine (0.3 g, 3.2 mmol) in THF (40 mL) at 5° C. After stirring for 10 minutes at 5° C., the mixture was warmed to room temperature and stirred overnight. The mixture was concentrated, and the residue was stirred with 1N HCl (30 mL) for 30 minutes. The solid was collected and slurried with hot acetone (15 mL) to give 1-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-3-o-tolyl-urea (0.7 g, 72%) as a white solid: mp>260° C.; 1H NMR (DMSO-d6) δ 2.05-2.09 (m, 1H), 2.19 (s, 3H), 2.49-2.65 (m, 2H), 2.84-2.98 (m, 1H), 4.73 (d, J=5.9 Hz, 2H), 5.13-5.20 (dd, J=5.4 and 12.7 Hz, 1H), 6.85-7.19 (m, 4H), 7.77-7.92 (m, 5H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 13.90, 17.99, 26.93, 34.68, 44.86, 116.73, 117.88, 118.14, 122.03, 123.05, 123.18, 126.06, 127.61, 129.69, 130.75, 133.93, '36.25, 151.47, 163.00, 163.56, 165.83, 168.76; Anal. calcd. for C22H20N4O5: C, 62.85; H, 4.79; N, 13.33. Found: C, 62.76; H, 4.75; N, 13.12.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated
  4. stirringthe residue was stirred with 1N HCl (30 mL) for 30 minutes
  5. customThe solid was collected

Sources & evidence

ORD record
ord-49c63d8d72e9420d81ede2f951d1d15a
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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