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Hydrogen Bromide → 2-(4-Hydroxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036689
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2036689
[ClH:1].C[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17]2[CH2:23][CH:24]4[NH:28][CH:27]([C:16]3=2)[CH2:26][CH2:25]4)(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br>C(O)(=O)C>[ClH:1].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17]2[CH2:23][CH:24]4[NH:28][CH:27]([C:16]3=2)[CH2:26][CH2:25]4)(=[O:12])=[O:11])=[CH:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 529129802-(4-Methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Produkt 1

HCID 529129822-(4-Hydroxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochlorideAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the product of Example 31, step B (18 mg, 0.04 mmol) and 33% HBr in acetic acid (10 mL) was heated at 60° C. for 4 days. The reaction mixture was concentrated in vacuo and the resulting residue neutralized with saturated sodium bicarbonate solution before extracting with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by semi-preparative HPLC and the free base treated with 1.25 M HCl methanol solution (0.5 mL) to give 2-(4-hydroxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (2 mg, 12%, AUC HPLC 97.2%) as an off-white solid: mp 210-212° C.; 1H NMR (CD3OD, 300 MHz) δ 8.18-8.23 (m, 1H), 7.73-7.81 (m, 2H), 7.69 (dd, J=9.0 Hz, 1.8 Hz, 1H), 7.55 (d, J=8.7 Hz, 1H), 6.82-6.90 (m, 2H), 5.25-5.36 (m, 1H), 4.53 (br s, 1H), 3.71 (s, 3H), 3.40-3.55 (m, 1H), 3.46-3.55 (m, 1H), 3.01-3.11 (m, 1H), 2.23-2.51 (m, 2H), 1.92-2.11 (m, 1H); ESI MS m/z 369 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionbefore extracting with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by semi-preparative HPLC
  7. additionthe free base treated with 1.25 M HCl methanol solution (0.5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-22ef8d0008b442e390558a2d897c89be
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575186B2

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