1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6,6-diphenyl-1 (2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amide

HRID 1243827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243827
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[Cl:25][CH2:26][CH2:27][NH2:28].[C:29]1([C:35]2([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH2:43][C:42]3[N:41]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[N:40]=[C:39]([C:52](O)=[O:53])[C:38]=3[CH:37]=[CH:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.C(N(CC)CC)C>[Cl:25][CH2:26][CH2:27][NH:28][C:52]([C:39]1[C:38]2[CH:37]=[CH:36][C:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH2:43][C:42]=2[N:41]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[N:40]=1)=[O:53]

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 97937372-Chloroethylamine hydrochlorideHCID 219287866,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid

Produkt 1

HCID 865940046,6-diphenyl-1 (2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amideAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

0.677 g of 1-hydroxybenzotriazole hydrate, 0.958 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1.16 g of 2-chloroethylamine hydrochloride and 1.4 cm3 of triethylamine are successively added to a solution of 1.8 g of 6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid in 300 cm3 of dichloromethane. After stirring the reaction mixture for about 4 hours at a temperature in the region of 20° C., it is washed with three times 60 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: cyclohexane/ethyl acetate (85/15 by volume)], 1.2 g of 6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amide are thus obtained in the form of a resin, the characteristics of which are as follows:

Aufarbeitung

  1. washis washed with three times 60 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-4bd1f3185be84872a4e733ec9d2b85c1
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119115B2

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