Ethoxyethylamine → 3'-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(2-ethoxyethyl)-4-biphenylcarboxamide

HRID 2426782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426782
CCN=C=NCCCN(C)C.Cl.[O:13]=[C:14]1[NH:18][C:17](=[O:19])[O:16][N:15]1[CH2:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH2:26][C:27]2[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([OH:41])=O)=[CH:35][CH:34]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1.[CH2:44]([O:46][CH2:47][CH2:48][NH2:49])[CH3:45].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[O:13]=[C:14]1[NH:18][C:17](=[O:19])[O:16][N:15]1[CH2:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH2:26][C:27]2[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([NH:49][CH2:48][CH2:47][O:46][CH2:44][CH3:45])=[O:41])=[CH:35][CH:34]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 66970EthoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577874453'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-4-biphenylcarboxylic acid

Produkt 1

HCID 577872243'-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(2-ethoxyethyl)-4-biphenylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

WSC hydrochloride (163 mg) was added to a mixture of 3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-4-biphenylcarboxylic acid (293 mg), (2-ethoxyethyl)amine (0.11 ml), HOBt (142 mg) and DMF (10 ml), followed by stirring at room temperature for 27 hours. The solvent was evaporated under a reduced pressure, and chloroform/methanol (4/1) was added to the residue, followed by washing with water and a saturated ammonium chloride aqueous solution. The solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol), the resulting foamy substance was further crystallized by adding diethyl ether, and the resulting crystals were recrystallized from methanol to obtain 3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(2-ethoxyethyl)-4-biphenylcarboxamide (135 mg) as white crystals.

Aufarbeitung

  1. customThe solvent was evaporated under a reduced pressure, and chloroform/methanol (4/1)
  2. additionwas added to the residue
  3. washby washing with water
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol)
  6. customthe resulting foamy substance was further crystallized
  7. additionby adding diethyl ether
  8. customthe resulting crystals were recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-944e929b6b424cbdb85f0fc7da3f6f2d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968552B2

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