1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

HRID 2189784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189784
[OH:1][NH:2][C:3](=[NH:20])[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:7]2.[C:21]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34])[C:26](O)=O)#[N:22].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:21]([C:23]1[CH:24]=[C:25]([C:26]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:7]4)[N:20]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:34])[CH3:35])#[N:22]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21956832RP-101124HCID 178471847HCID 178471847, Verbindung

Produkt 1

HCID 59316802Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (265 mg, 0.96 mmol), 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (197 mg, 0.96 mmol), EDAC (203 mg) and HOBt (142 mg) were stirred in DMF (5 ml) at 80° C. for 2 hours. Stirred at room temperature over the weekend, then heated at 80° C. for a further 4 hours. The reaction mixture was cooled and then partitioned between EtOAc and sodium bicarbonate. The organic layer was separated, washed with brine, dried and evaporated to dryness in vacuo. The crude material was purified by flash chromatography to afford the title compound (214 mg) as a white solid. MS (ES): C24H23N5O4 requires 445; found (MH+) 446.

Aufarbeitung

  1. temperatureheated at 80° C. for a further 4 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between EtOAc and sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. customevaporated to dryness in vacuo
  8. customThe crude material was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0fffe130320d47808cfd37f02e18e784
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324254B2

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