2-Aminoindane → HCID 58276358, Verbindung

HRID 471870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471870
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=3)=[CH:14][CH:13]=2)=[N:8]1)=[O:4].[NH2:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C1COCC1.CO>C(O)(=O)C>[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:28][CH:29]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30]4)[CH:19]=3)=[CH:16][CH:17]=2)=[N:8]1)=[O:4]

Komponenten

5

Edukt 3

HCID 763102-AminoindaneHCID 21899815MeOH tetrahydrofuranHCID 58276410HCID 58276410, Verbindung

Produkt 1

HCID 58276358HCID 58276358, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of [3-(3′-formyl-4-biphenylyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.081 g, 0.22 mmol; I-X-17) and 2-aminoindane (0.045 mL, 0.35 mmol) in 1:1 THF/MeOH (2 mL) was added acetic acid (0.12 mL) and MP-BH3CN (ca. 0.67 mmol, Note 1). The mixture was stirred at room temperature overnight, resin was remove by filtration (THF wash) and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc/5% Na2CO3, layers were separated and the aqueous layer was extracted with EtOAc. Combined organics were washed (water, brine), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (MeOH/CH2Cl2), affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (s, 9H), 2.84 (dd, J=15.6, 6.4 Hz, 2H), 3.20 (dd, J=15.6, 7.1 Hz, 2H), 3.68-3.75 (m, 1H), 3.93 (s, 2H), 6.09 (s, 2H), 7.08-7.23 (m, 4H), 7.31-7.38 (m, 1H), 7.41 (t, J=7.6 Hz, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.63 (s, 1H), 7.69 (d, J=8.3 Hz, 2H), 8.19 (d, J=8.3 Hz, 2H), 8.37 (s, 1H).

Aufarbeitung

  1. customresin was remove by filtration (THF wash)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc/5% Na2CO3, layers
  4. customwere separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washCombined organics were washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-fb2b1e1759b4456fb2aa9441afec21d4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633175B2

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