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Trifluoroacetic acid → 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

HRID 1514262
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514262
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].FC(F)(F)C(O)=O>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 594034711,1-Dimethylethyl 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Produkt 1

HCID 684679086-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochlorideAusbeute 199,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 17) (260 mg, 0.537 mmol) was dissolved in DCM (20 ml) and treated with trifluoroacetic acid (2 ml, 26.0 mmol). The resulting mixture was heated at reflux for 1 hour then evaporated. The resulting residue was partitioned between DCM (10 ml) and 2N NaOH (10 ml). The DCM layer was collected, dried (hydrophobic frit) and evaporated. The free-base was dissolved in 4M HCl in dioxane and evaporated to give the HCl salt, 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (225 mg, 0.535 mmol, 100% yield) as an off-white powder. δH (400 MHz, CDCl3) 10.10 (2H, br.s), 8.18 (1H, s), 8.02 (1H, d), 7.82-7.80 (1H, m), 7.33-7.22 (2H, m), 7.05 (1H, d), 5.30 (2H, s), 4.76-4.64 (1H, m), 3.8-3.65 (2H, m), 3.48-3.3 (4H, m), 1.45 (6H, d); MS (ES) C21H2235ClN3O2 requires 383; found 384 [M+H]+.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthen evaporated
  4. customThe resulting residue was partitioned between DCM (10 ml) and 2N NaOH (10 ml)
  5. customThe DCM layer was collected
  6. customdried (hydrophobic frit)
  7. customevaporated
  8. dissolutionThe free-base was dissolved in 4M HCl in dioxane
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-46e32b24074a46ba9885043cab92f365
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222245B2

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