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Ammonium Chloride → 3-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 1992624
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Reaktionsgleichung

Reaktionsgleichung von HRID 1992624
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:7][CH:8]=2)[C:3]=1[CH2:16][C:17]([NH2:19])=[O:18].C[O:21][C:22](=O)[C:23]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]([CH3:14])[CH3:15])=[CH:7][CH:8]=2)[C:3]=1[C:16]1[C:17](=[O:18])[NH:19][C:22](=[O:21])[C:23]=1[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1
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Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 44536752-(1-Methyl-1H-indol-3-YL)-2-oxoacetic acid methyl esterHCID 23665647Potassium tert-butoxideHCID 668697562-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-acetamide

Produkt 1

HCID 536308903-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Activated 3 Å molecular sieve (2.0 g) is added to a solution of 2-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-acetamide (1.0 g, 3.61 mmol) and (1-Methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (1.02 g, 4.69 mmol) in dry THF (50 ml) under an atmosphere of argon. A solution of 1.0 M KOtBu in THF (10.9 ml, 10.9 mmol) is then added in one portion at RT. After 1 h at RT, TLC analysis indicates complete conversion of starting materials. The reaction mixture is diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. The organic layer is separated, washed with brine, dried over Na2SO4, and the organic solvent is evaporated. The residue is purified by FCC (EtOAc/AcOH/H2O 600:150:150) to afford the title compound, which is dissolved in glacial AcOH and lyophilized. The title compound is obtained as the water soluble bis-acetate salt. 1H NMR (d6-DMSO, 400 MHz): δ 1.80 (s, 6H), 3.20-3.42 (m, 2H), 6.10 (d, J=9.0 Hz, 1H), 6.44 (t, J=9.0 Hz, 1H), 6.94 (t, J=9.0 Hz, 1H), 7.31 (d, J=9.0 Hz, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.42 (s, 1H), 7.63 (d, J=10.8 Hz, 1H), 7.89 (d, J=9.6 Hz, 1H), 8.03 (d, J=9.0 Hz, 1H), 8.10 (s, 1H), 11.0-11.3 (br, 1H). ES+−MS: 444, 446 [M+H]+.

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe organic solvent is evaporated
  5. customThe residue is purified by FCC (EtOAc/AcOH/H2O 600:150:150)

Quellen und Nachweise

ORD-Eintrag
ord-b1ee804370f74f2698dd2c4246233c2c
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07648989B2

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