Triethylamine → HCID 16117341, compound

HRID 448291Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][N:14]([CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[NH:23][C:22]1=[O:28])[C:15]2=[O:20].Cl.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C1COCC1>[O:28]=[C:22]1[CH:21]([N:14]2[CH2:13][C:12]3[C:16](=[CH:17][CH:18]=[CH:19][C:11]=3[CH2:10][NH:9][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[C:15]2=[O:20])[CH2:26][CH2:25][C:24](=[O:27])[NH:23]1

Participants

Conditions

Temperature: 5 °C

Procedure

Triethylamine (0.7 g, 7.4 mmol) was added to a stirred suspension of 3-(4-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.7 g, 2.1 mmol) and isonicotinoyl chloride hydrochloride (0.5 g, 2.5 mmol) in THF (30 mL) at 5-10° C. After stirring for 10 minutes at 5° C., the mixture was stirred at room temperature overnight. The mixture was filtered, and the solid was slurried with hot methanol (30 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-isonicotinamide (0.5 g, 63%): mp 282-284° C.; 1H NMR (DMSO-d6) δ 2.01-2.06 (m, 1H), 2.38-2.66 (m, 2H), 2.86-2.98 (m, 1H), 4.41-4.64 (m, 4H, 2CH2), 5.12-5.19 (dd, J=4.6 and 13.0 Hz, 1H, CH), 7.48-7.67 (m, 3H, Ar), 7.78-7.80 (d, J=4.8 Hz, 2H, Ar), 8.73-8.75 (m, d, J=4.8 Hz, 2H, Ar), 9.39 (s, 1H, NH), 11.03 (s, 1H, NH); 13C NMR (DMSO-d6) δ 22.59, 31.18, 39.67, 46.27, 51.61, 121.25, 121.83, 128.38, 130.76, 131.68, 134.11, 140.24, 140.98, 150.27, 164.87, 168.03, 171.00, 172.84; Anal. calcd. for C20H18N4O4: C, 63.49; H, 4.79; N, 14.81. Found: C, 63.22; H, 4.73; N, 14.62.

Workup

stirringthe mixture was stirred at room temperature overnight
filtrationThe mixture was filtered

Sources & evidence

ORD record: ord-e5eacd0c44024e9b8b00808cfda98fc1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481568B2

Reaction notes

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