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2,3-Dimethylaniline → tert-butyl 6-[2-(2,3-dimethylanilino)-2-oxoethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

HRID 1071047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1071047
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:22][C:23](O)=[O:24])[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29].CN(C1C=CC=CN=1)C.C(N=C=NC(C)C)(C)C>C1COCC1.CCOC(C)=O>[CH3:26][C:27]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:23](=[O:24])[CH2:22][N:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH2:20][CH2:21][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][C:11]1=2
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Komponenten

7

Edukt 4

HCID 68932,3-DimethylanilineHCID 12734DiisopropylcarbodiimideHCID 218852-DimethylaminopyridineHCID 22396950(3-(tert-butoxycarbonyl)-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetic acid

Produkt 1

HCID 22396686tert-butyl 6-[2-(2,3-dimethylanilino)-2-oxoethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate
Ausbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3-(tert-butoxycarbonyl)-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetic acid (3.38 mmol) was dissolved in THF (20 mL) and 2,3-dimethylaniline (0.43 mL, 0.43 g, 3.6 mmol, 1.05 equiv.), dimethylaminopyridine (0.415 g, 3.40 mmol, 1.01 equiv.), and diisopropylcarbodiimide (0.60 mL, 0.48 g, 3.8 mmol, 1.13 equiv.) were added. The reaction mixture was stirred at rt under N2 for 18 h. The reaction mixture was taken up in EtOAc (100 mL) and this solution was washed with 10% aqueous citric acid (2×50 mL), 5% aqueous NaHCO3 (2×50 mL), and brine (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The crude product (1.7223 g) was chromatographed (SiO2 187 g, eluted with 10:1 toluene:acetone followed by 9:1 toluene:acetone) to give tert-butyl 6-[2-(2,3-dimethylanilino)-2-oxoethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (1.1066 g) in 67% yield. 1H NMR (300 MHz, CD3OD) δ 1.50, 2.01-2.03, 2.27, 2.29-3.12, 3.66-3.75, 3.75-3.83, 5.03, 7.04-7.19, 7.37, 7.49; MS (ESI+) for C27H33N3O3 m/z 448.1 (M+H)+.

Aufarbeitung

  1. washthis solution was washed with 10% aqueous citric acid (2×50 mL), 5% aqueous NaHCO3 (2×50 mL), and brine (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product (1.7223 g) was chromatographed
  6. wash(SiO2 187 g, eluted with 10:1 toluene:acetone followed by 9:1 toluene:acetone)

Quellen und Nachweise

ORD-Eintrag
ord-6b89643ebfd24ae18f0f4b3f032c6397
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06903090B2

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