Triethylamine → HCID 86611119, compound

HRID 448454Notes

Reaction equation

HRID 448454 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:22])[N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13].C(N(CC)CC)C.[C:30]1([C:36]2[O:40][C:39]([C:41](Cl)=[O:42])=[N:38][N:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC#N>[C:30]1([C:36]2[O:40][C:39]([C:41]([OH:42])=[O:13])=[N:38][N:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[O:21]=[C:15]1[CH:14]([N:7]2[C:6](=[O:22])[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[CH2:3][NH-:2])[C:8]2=[O:13])[CH2:19][CH2:18][C:17](=[O:20])[NH:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27796565-Phenyl-1,3,4-oxadiazole-2-carbonyl chlorideHCID 219885254-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 2

HCID 233586875-Phenyl-1,3,4-oxadiazole-2-carboxylic acidHCID 86611119HCID 86611119, compoundYield 195%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-aminomethyl-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (1.55 g, 4.8 mmol) in CH3CN (15 ml), was added triethyl amine (1.67 mL, 11.98 mmol) and 5-phenyl-1,3,4-oxadiazole-2-carbonyl-chloride (1.0 g, 4.8 mmol). The mixture was stirred at room temperature for 21 hours and a suspension was obtained. The reaction mixture was filtered, and the solid was rinsed with CH3CN (20 mL), water (2×20 mL), EtOAc (20 mL) and MeOH (20 mL) to afford 5-phenyl-[1,3,4]oxadiazole-2-carboxylic acid [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethylamide as a white solid (1.34 g, 61%): mp, 279-281° C.; HPLC: Waters Symmetry C-18, 3.9×150 mm, 5 micro, 1 mL/min, 240 nm, 40/60 (CH3CN/H2O): tR=4.90 min. (99%); 1H NMR (DMSO-d6): δ 2.08-2.10 (m, 1H), 2.53-2.64 (m, 2H), 2.86-2.98 (m, 1H), 4.98 (d, J=5 Hz, 1H), 5.18 (dd, J=5, 13 Hz, 1H), 7.62-7.72 (m, 3H), 7.85 (broad, 3H), 8.09-8.12 (m, 2H). 9.97 (t, J=5 Hz, 1H), 11.15 (s, 1H). 13C NMR (DMSO-d6) δ: 21.90, 30.85, 38.24, 48.82, 122.07, 122.70, 126.98, 127.16, 129.46, 131.49, 132.58, 133.03, 134.77, 137.63, 153.51, 158.29, 164.94, 166.84, 167.42, 169.74, 172.67. Anal Calcd for C23H17N5O6: C, 60.13; H, 3.73; N, 15.24. Found: C, 56.69; H, 3.34; N, 15.41.

Workup

  1. customa suspension was obtained
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was rinsed with CH3CN (20 mL), water (2×20 mL), EtOAc (20 mL) and MeOH (20 mL)

Sources & evidence

ORD record
ord-a43386a3ac7e4daea752a0a633aeadee
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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