1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58827340, compound

HRID 448430Notes

Reaction equation

HRID 448430 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:33])[N:18]([CH:25]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24].O=C1CCC(=O)N1[O:41][C:42](=O)[NH:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>C(#N)C>[O:32]=[C:26]1[CH:25]([N:18]2[C:17](=[O:33])[C:16]3[C:20](=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14][NH:13][C:42]([NH:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)=[O:41])[C:19]2=[O:24])[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219885254-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochlorideHCID 86611118HCID 86611118, compound

Product 1

HCID 58827340HCID 58827340, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.4 g, 2.4 mmol) was added to a stirred suspension of 4-aminomethyl-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (0.7 g, 2.0 mmol) in acetonitrile (50 mL). After stirring for 30 minutes, pyridin-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl ester (0.7 g, 3.0 mmol) was added, and the mixture was stirred at room temperature overnight. The solid was collected and slurried with hot acetone (20 mL) to give 1-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-3-pyridin-2-yl-urea (0.5 g, 64%) as a white solid: mp>260° C.; 1H NMR (DMSO-d6) δ 2.05-2.09 (m, 1H), 2.49-2.65 (m, 2H), 2.84-2.79 (m, 1H), 4.83 (d, J=6.1 Hz, 2H), 5.14-5.21 (dd, J=5.5 and 12.7 Hz, 1H), 6.91-6.96 (m, 1H), 7.33 (d, J=8.5 Hz, 1H), 7.64-7.88 (m, 4H), 8.17-8.20 (dd, J=1.3 and 5.0 Hz, 1H), 8.90 (t, J=5.7 Hz, 1H), 9.44 (s, 1H), 11.16 (s, 1H); 13C NMR (DMSO-d6) δ 21.96, 30.92, 38.67, 48.85, 93.31, 111.57, 116.91, 121.90, 127.20, 131.67, 133.43, 134.80, 138.23, 139.82, 146.69, 153.27, 154.93, 166.97, 167.49, 169.81, 172.75; Anal. calcd. for C20H17N5O5: C, 58.97; H, 4.21; N, 17.19. Found: C, 58.69; H, 4.10; N, 17.05.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solid was collected

Sources & evidence

ORD record
ord-dc24550ff10b4e2fbf968d4cf1a90ca0
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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