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

HRID 2037375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037375
[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]([N:68]([CH2:70][C:71](O)=[O:72])C)(OC(C)(C)C)=O>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:71](=[O:72])[CH2:70][NH:68][CH3:61])[CH3:2]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 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 68628912n-(2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-methylamino-acetamideAusbeute 38,9 %

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 BOC-sarcosine (26 mg, 139 μmol) is added. The mixture is stirred at rt for 1 h before it is concentrated. The residue is dissolved in 4 M HCl in dioxane (2 mL) and the mixture is stirred at rt for 30 min, concentrated and separated by prep. HPLC to give the title compound (23 mg) as a reddish oil; LC-MS: tR=0.89 min, [M+H]+=466.05.

Aufarbeitung

  1. concentrationis concentrated
  2. dissolutionThe residue is dissolved in 4 M HCl in dioxane (2 mL)
  3. stirringthe mixture is stirred at rt for 30 min
  4. concentrationconcentrated
  5. customseparated by prep

Quellen und Nachweise

ORD-Eintrag
ord-d03eb189d5d14c48b7ee35dcdd3f242e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

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