Diisopropylethylamine → HCID 69157953, Verbindung

HRID 1057514

Reaktionsgleichung

Reaktionsgleichung von HRID 1057514
[ClH:1].[C:2]([O:5][CH2:6]C)(=[O:4])[CH3:3].[C:8](Cl)(Cl)=[O:9].[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:19]1[C:24]2=[N:25][C:26]([CH2:29][CH2:30][CH2:31][NH2:32])=[CH:27][CH:28]=[C:23]2[CH2:22][CH2:21][CH2:20]1.C([N:36]([CH2:40][CH3:41])[CH:37]([CH3:39])C)(C)C>>[Cl:1][C:17]1[CH:12]=[CH:13][C:14]2[CH:15]([CH2:3][C:2]([O:5][CH3:6])=[O:4])[CH2:41][CH2:40][N:36]([C:8](=[O:9])[NH:32][CH2:31][CH2:30][CH2:29][C:26]3[N:25]=[C:24]4[NH:19][CH2:20][CH2:21][CH2:22][C:23]4=[CH:28][CH:27]=3)[CH2:37][C:39]=2[CH:16]=1

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amineHCID 19083224Phosgen tolueneHCID 21866389Hydrogen chloride-ethyl acetate

Produkt 1

HCID 69157953HCID 69157953, Verbindung

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of methyl 2-{2-[(tert-butyl)oxycarbonyl-8-chloro-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate (1 eq) in 1.17 M of HCl/ethyl acetate (30 eq) was stirred at room temperature for 18 hr. The reaction mixture was concentrated and dried under vacuum oven. The resulting residue was dissolved in methylene chloride (0.15 M) and followed by the addition of phosgene/toluene (20%) (10 eq) under nitrogen. After stirring for 1 hr, the solvent was removed by rotary evaporation. The residue was dissolved in 1 ml of N,N-dimethylformamide (0.07 M), followed by the addition of 3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propylamine (2 eq) and N,N-diisopropylethylamine (10 eq). The reaction mixture was heated at 50° C. for 2 hr. The reaction solvent was removed by rotary evaporation and the residue was purified by flash chromatography (5% methanol/methylene chloride. EI-MS m/z 471 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum oven
  3. dissolutionThe resulting residue was dissolved in methylene chloride (0.15 M)
  4. customthe solvent was removed by rotary evaporation
  5. dissolutionThe residue was dissolved in 1 ml of N,N-dimethylformamide (0.07 M)
  6. customThe reaction solvent was removed by rotary evaporation
  7. customthe residue was purified by flash chromatography (5% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-72527742638549a38e123850f576bf01
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514964B1

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