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1,2-Dichloroethane → Ethyl (+/-)-10,11-dihydro-3-[[[2-(2-pyridylamino)ethyl]amino]carbonyl]-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 613390
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Reaktionsgleichung

Reaktionsgleichung von HRID 613390
C(Cl)CCl.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[CH2:13][C:12]=2[CH:28]=1)(O)=[O:6].Cl.Cl.[NH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][CH2:33][CH2:32][NH:31][C:5]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[CH2:13][C:12]=2[CH:28]=1)=[O:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 14238461N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)HCID 15516628Ethyl (+/-)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Produkt 1

HCID 54300392Ethyl (+/-)-10,11-dihydro-3-[[[2-(2-pyridylamino)ethyl]amino]carbonyl]-5H-dibenzo[a,d]cycloheptene-10-acetateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (112.7 mg, 0.59 mmole) was added all at once to a solution of ethyl (±)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate (157.8 mg, 0.49 mmole), 2-[(2-aminoethyl)amino]pyridine dihydrochloride (123.5 mg, 0.59 mmole), HOBt.H2O (79.5 mg, 0.59 mmole), and diisopropylethylamine (0.43 mL, 2.45 mmole) in anhydrous DMF (2.5 mL) at RT. The reaction was stirred at RT for 18 hr, then was concentrated. The residue was reconcentrated from xylenes, then was diluted with H2O (5 mL) and extracted sequentially with EtOAc (2×5 mL) and CHCl3 (2×5 mL). The organic layers were combined and treated with a little MeOH to dissolve a small amount of insoluble material. Drying (MgSO4), concentration, and silica gel chromatography (5% MeOH/CHCl3) gave the title compound (199.1 mg, 92%) as a yellow oil: TLC (5% MeOH/CHCl3) Rf 0.42; 1H NMR (400, CDCl3) δ 8.10 (d, J=3.5 Hz, 1 H), 8.02 (br s, 1 H), 7.60 (app. narrow d, 1 H), 7.53 (app. dd, 1 H), 7.33-7.42 (m, 1 H), 7.08-7.22 (m, 5 H), 6.57-6.65 (m, 1 H), 6.45 (d, J=8.3 Hz, 1 H), 4.79-4.90 (m, 1 H), 4.36 (d,J=15.1 Hz, 1 H), 4.11-4.26 (m, 2 H), 3.92 (d, J=15.1 Hz, 1 H), 3.80-3.95 (m, 1 H), 3.55-3.72 (m, 4 H), 3.38 (dd, J=15.2, 4.1 Hz, 1 H), 3.03 (dd, J=15.2, 9.5 Hz, 1 H), 2.66 (dd, J=15.8,4.8 Hz, 1 H), 2.50 (dd, J=15.8, 9.6 Hz, 1 H), 1.27 (t, J=7.2 Hz, 3 H); MS (ES) m/e 444 (M+H)+.

Aufarbeitung

  1. customat RT
  2. concentrationwas concentrated
  3. additionwas diluted with H2O (5 mL)
  4. extractionextracted sequentially with EtOAc (2×5 mL) and CHCl3 (2×5 mL)
  5. additiontreated with a little MeOH
  6. dissolutionto dissolve a small amount of insoluble material
  7. customDrying
  8. concentration(MgSO4), concentration, and silica gel chromatography (5% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-d56b59534d314cb2b7c69255d7a3e17d
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06008213

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