Dimethylformamide → 5-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

HRID 423294

Reaktionsgleichung

Reaktionsgleichung von HRID 423294
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=O.[CH:15]1[CH:16]=[CH:17][C:18]2N(O)N=[N:21][C:19]=2C=1.CCN=C=N[CH2:30][CH2:31][CH2:32][N:33]([CH3:35])C.C[N:37](C=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:21]=[C:19]([C:18]3[CH:17]=[C:16]4[C:32](=[CH:31][CH:30]=3)[NH:33][CH:35]=[CH:15]4)[N:37]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acid

Produkt 1

HCID 593183535-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

D4 (7.55 g), HOBT (5.23 g) and EDCI (7.42 g) were dissolved in DMF (88 ml). This mixture was stirred for 10 minutes and then the yellow-orange solid from above (6.16 g) dissolved in DMF (88 ml) was added. The reaction mixture was heated to 80° C. overnight then evaporated and partitioned between EtOAc and H2O. The phases were separated and the aqueous solution extracted with two further portions of EtOAc. The combined organic solutions were dried and evaporated. Part of the crude residue was purified on a 40+M Biotage cartridge, eluting with a 5-30% mixture of EtOAc in hexane. This gave the title compound (1.45 g) as an off-white solid. δH (CDCl3, 400 MHz): 1.45 (6H, d), 4.72 (1H, septet), 6.66-6.69 (1H, m), 7.06 (1H, d), 7.29 (1H, apparent triplet or dd), 7.50 (1H, d), 8.01 (1H, dd), 8.08 (1H, dd), 8.27 (1H, d), 8.49-8.52 (1H, m). MS (ES): C19H16ClN3O2 requires 353; found 354 (MH+). The remaining crude reside was triturated with cold MeOH to give the title compound (3.54 g) as an off white solid. MS data as above.

Aufarbeitung

  1. additionwas added
  2. customthen evaporated
  3. custompartitioned between EtOAc and H2O
  4. customThe phases were separated
  5. extractionthe aqueous solution extracted with two further portions of EtOAc
  6. customThe combined organic solutions were dried
  7. customevaporated
  8. customPart of the crude residue was purified on a 40+M Biotage cartridge
  9. washeluting with a 5-30% mixture of EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-1bae2ca04aba4e5c932bad7e9d2092a3
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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