Acetonitrile → 1-(2-Methoxy-5-tetrazol-1-yl-phenyl)-1-[(R)-3-phenyl-3-(2-{4-[1-(2-pyrazol-1-yl-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepan-1-yl}-ethyl)-pyrrolidin-1-yl]-methanone

HRID 2230719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230719
I.I.[N:3]1([C:10]2[N:14]([CH2:15][CH2:16][N:17]3[CH:21]=[CH:20][CH:19]=[N:18]3)[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]=2)[CH2:9][CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[N:37][N:36]=[N:35]2)=[CH:30][C:29]=1[C:39]([N:41]1[CH2:45][CH2:44][C@:43]([CH2:52][CH2:53]OS(C)(=O)=O)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:42]1)=[O:40].C(N(C(C)C)CC)(C)C.C(#N)C>ClCCl>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[N:37][N:36]=[N:35]2)=[CH:30][C:29]=1[C:39]([N:41]1[CH2:45][CH2:44][C@@:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([CH2:52][CH2:53][N:6]2[CH2:7][CH2:8][CH2:9][N:3]([C:10]3[N:14]([CH2:15][CH2:16][N:17]4[CH:21]=[CH:20][CH:19]=[N:18]4)[C:13]4[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=4[N:11]=3)[CH2:4][CH2:5]2)[CH2:42]1)=[O:40]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 184648602-[1,4]diazepan-1-yl-1-(2-pyrazol-1-yl-ethyl)-1H-benzoimidazole dihydroiodideHCID 86583904HCID 86583904, Verbindung

Produkt 1

HCID 599022731-(2-Methoxy-5-tetrazol-1-yl-phenyl)-1-[(R)-3-phenyl-3-(2-{4-[1-(2-pyrazol-1-yl-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepan-1-yl}-ethyl)-pyrrolidin-1-yl]-methanoneAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Reflux a mixture of 2-[1,4]diazepan-1-yl-1-(2-pyrazol-1-yl-ethyl)-1H-benzoimidazole dihydroiodide (0.48 g, 0.84 mmol), methanesulfonic acid 2-{(S)-1-[1-(2-methoxy-5-tetrazol-1-yl-phenyl)-methanoyl]-3-phenyl-pyrrolidin-3-yl}-ethyl ester (0.40 g, 0.84 mmol, example 47.2), diisopropylethylamine (0.44 g, 3.37 mmol) and acetonitrile (20 mL) for 12 hours. Cool and dilute with dichloromethane (150 mL), wash the organic phase with water (2×10 mL), dry (MgSO4) the organic phase, filter and evaporate. Purify the residue by silica gel chromatography eluting with 0.5% methanol in dichloromethane to afford 0.29 g of the title compound, Rf=0.18 (silica gel, 0.5% methanol in dichloromethane). The compound may be converted to the dihydrochloride salt by methods well known in the art.

Aufarbeitung

  1. temperatureReflux
  2. temperatureCool
  3. washwash the organic phase with water (2×10 mL)
  4. dry with materialdry (MgSO4) the organic phase
  5. filtrationfilter
  6. customevaporate
  7. customPurify the residue by silica gel chromatography
  8. washeluting with 0.5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fb211f43fdf84ccab88209a53133e171
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423704B1

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