Glycolic Acid → n-(2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-hydroxy-acetamide

HRID 2037374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037374
[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:20][N:19]=3)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:29])[C:4]=1[O:5][CH2:6][CH2:7][NH2:8])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:61](O)(=[O:64])[CH2:62][OH:63]>C1COCC1.CN(C=O)C>[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:20][N:19]=3)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:29])[C:4]=1[O:5][CH2:6][CH2:7][NH:8][C:62](=[O:63])[CH2:61][OH:64])[CH3:2]

Komponenten

8

Edukt 5

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 442181592-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethylamine

Produkt 1

HCID 44218161n-(2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-hydroxy-acetamideAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the compound of Example 48 (50 mg, 127 μmol) in THF (2 mL) and DMF (2 mL), EDC hydrochloride (27 mg, 139 μmol), HOBt (19 mg, 139 μmol), DIPEA (25 mg, 190 μmol) and glycolic acid (11 mg, 139 μmol) is added. The mixture is stirred at rt for 1 h before it is concentrated and separated by prep. HPLC to give the title compound (32 mg) as a colourless oil; LC-MS: tR=1.05 min, [M+H]+=453.08; 1H NMR (CDCl): δ1.00 (d, J=6.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.89-2.00 (m, 1H), 2.37 (s, 3H), 2.47 (s, 3H), 2.63 (d, J=7.0 Hz, 2H), 2.73 (q, J=7.5 Hz, 2H), 3.75-3.83 (m, 2H), 3.93-3.99 (m, 2H), 4.23 (s, 2H), 7.03-7.15 (m, 1H), 7.94 (s, 2H), 8.09 (s, 1H), 8.55 (s, 1H).

Aufarbeitung

  1. concentrationis concentrated
  2. customseparated by prep

Quellen und Nachweise

ORD-Eintrag
ord-3d6f464e7d2b4ddb96ea8ddadb6e483d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

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