1,2-Dichloroethane → Ethyl (+/-)-10,11-dihydro-3-[[[(1H-benzimidazol-2-yl)methyl]methylamino]carbonyl]5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 613382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613382
[CH2:1](Cl)[CH2:2]Cl.[C:5]([C:8]1C=C[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]C=CC=3C[C:12]=2[CH:28]=1)(O)=[O:6].Cl.Cl.[CH3:31][NH:32][CH2:33][C:34]1[NH:35][C:36]2[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=2[N:38]=1.[CH:43]1[CH:44]=CC2N(O)N=N[C:47]=2[CH:48]=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH:38]1[C:37]2[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=2[N:35]=[C:34]1[CH2:33][N:32]([CH3:31])[C:5]([C:8]1[CH:28]=[CH:12][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:44]=[CH:43][C:48]=3[CH2:47][C:1]=2[CH:2]=1)=[O:6]

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13169407((1H-1,3-benzodiazol-2-yl)methyl)(methyl)amine dihydrochlorideHCID 15516628Ethyl (+/-)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Produkt 1

HCID 54459000Ethyl (+/-)-10,11-dihydro-3-[[[(1H-benzimidazol-2-yl)methyl]methylamino]carbonyl]5H-dibenzo[a,d]cycloheptene-10-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (202.4 mg, 1.06 mmol) was added all at once to a solution of ethyl (±)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate (285.6 mg, 0.88 mmol), 2-(methylamino)methylbenzimidazole dihydrochloride (247.2 mg, 1.06 mmol), HOBt.H2O (142.7 mg, 1.06 mmol), and diisopropylethylamine (0.61 mL, 3.52 mmol) in anhydrous DMF (4.4 mL) at RT. The reaction was stirred at RT for 16.5 h, then was concentrated on the rotavap (high vacuum). The residue was reconcentrated from xylenes, then was dissolved in H2O (5 mL). EtOAc extraction (2×5 mL), drying (MgSO4), concentration, and chromatography (silica gel, 5% MeOH in 1:1 EtOAc/CHCl3) gave the title compound as a faintly yellow foam (389.2 mg, 95%): TLC Rf (10% MeOH in 1:1 EtOAc/CHCl3) 0.60; 1H NMR (400 MHz, CDCl3) δ 7.70-7.80 (m, 1H), 7.40-7.50 (m, 1H), 7.35 (s, 1H), 7.21-7.32 (m, 3H), 7.04-7.21 (m, 5H), 4.76-4.88 (m, 2H), 4.36 (d, J=15.2 Hz, 1H), 4.18 (q, J=7.1 Hz, 2H), 3.90 (d, J=15.2 Hz, 1H), 3.82-3.95 (m, 1H), 3.38 (dd, J=15.4, 4.0 Hz, 1H), 3.11 (s, 3H), 3.03 (dd, J=15.4, 9.5 Hz, 1H), 2.69 (dd, J=15.8, 4.8 Hz, 1H), 2.52 (dd, J=15.8, 9.6 Hz, 1H), 1.27 (t, J=7.1 Hz, 3H); FTIR (CCl4) 2700-3470 (broad), 1735, 1629 (shoulder), 1617, 1484, 1454, 1422, 1397, 1271, 1180, 1157 cm-1 ; MS (ES) m/e 468.2 (M+H)+.

Aufarbeitung

  1. customat RT
  2. concentrationwas concentrated on the rotavap (high vacuum)
  3. dissolutionwas dissolved in H2O (5 mL)
  4. extractionEtOAc extraction (2×5 mL)
  5. customdrying
  6. concentration(MgSO4), concentration, and chromatography (silica gel, 5% MeOH in 1:1 EtOAc/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-b9d1d29a4e024eb584bf6dbba0c21b2a
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008213

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