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tert-Butyl acrylate → 3-[7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]propanoic acid

HRID 1514273
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514273
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11].[C:29]([O:33]C(C)(C)C)(=[O:32])[CH:30]=[CH2:31].C(N(C(C)C)CC)(C)C>CO>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][N:24]([CH2:31][CH2:30][C:29]([OH:33])=[O:32])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11]
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Komponenten

5

Edukt 3

HCID 15458tert-Butyl acrylateHCID 81531DiisopropylethylamineHCID 684687897-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

Produkt 1

HCID 426364333-[7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]propanoic acidAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (Example 17) (200 mg, 0.52 mmol), 1,1-dimethylethyl 2-propenoate (151 μL, 1.04 mmol) and diisopropylethylamine (453 μL, 2.60 mmol) in methanol (5 ml) was heated in the microwave at 90° C. for 30 minutes before the solvent was removed in vacuo. The residue was dissolved in 4M HCl (2 ml) in dioxane and the mixture stirred at room temperature for 5 h. The solvent was removed in vacuo and the residue purified by MDAP. To the product containing fractions was added 2M HCl and the solution concentrated in vacuo to give the title compound as a white solid (116 mg, 0.24 mmol). δH (d6DMSO, 400 MHz): 12.73 (1H, br.s), 10.76 (1H, br.s), 8.19 (1H, d), 8.11 (1H, dd), 7.98 (1H, d), 7.93 (1H, dd), 7.46 (1H, d), 7.45 (1H, d), 4.89 (1H, septet), 3.76-3.64 (2H, m), 3.44-3.31 (4H, hidden under H2O peak), 3.25-3.03 (4H, m), 2.89 (2H, t), 1.37 (6H, d). MS (ES): C24H2635ClN3O4 requires 455; found 456 [M+H]+.

Aufarbeitung

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in 4M HCl (2 ml) in dioxane
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by MDAP
  5. additionTo the product containing fractions
  6. additionwas added 2M HCl
  7. concentrationthe solution concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-535cf69fae874a1bbf7d94e0b7d675a3
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222245B2

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