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1,2-Dichloroethane → (E)-N-methyl-N-(2-methyl-1H-indol-3-yl methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide

HRID 18334
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 18334
[CH2:1](Cl)[CH2:2]Cl.Cl.[O:6]=[C:7]1[NH:13][C:12]2[N:14]=[CH:15][C:16](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:17][C:11]=2[CH2:10][CH2:9][CH2:8]1.[CH3:23][C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH2:33][NH:34][CH3:35])=[CH:30][CH:29]=[CH:28][CH:27]=2.[CH:36]1C=CC2N(O)N=NC=2C=1.[OH2:46].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:36][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:31][CH2:32][CH2:24][CH2:23][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:17]=[CH:16]/[CH2:18][CH:19]1[C:20](=[O:21])[O:22][C:2](=[O:46])[CH2:1]1.[CH3:35][N:34]([CH2:33][C:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:23])[C:20](=[O:22])/[CH:19]=[CH:18]/[C:16]1[CH:15]=[N:14][C:12]2[NH:13][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:17]=1
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Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905085(E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride

Produkt 2

HCID 5363103
2,5-Furandione, dihydro-3-(2-octadecen-1-yl)-
HCID 10023175(E)-N-methyl-N-(2-methyl-1H-indol-3-yl methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamideAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (0.18 g, 0.96 mmole) was added to a solution of (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride salt (0.24 g, 0.87 mmole), 2-methyl-3-(methylaminomethyl)indole (0.15 g, 0.87 mmole), HOBt H2O (0.13 g., 0.96 mmole) and diisopropylethylamine (0.45 mL, 2.61 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Preparative HPLC on a Waters C-18 ODSA column (gradient: 20-100% H2O/CH3CN) gave the title compound (0.13 g, 38%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Aufarbeitung

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-3a6af946cc7a4546a338c94184e70f94
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741339B2

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