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 1243827Notes

Reaction equation

HRID 1243827 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 865940046,6-diphenyl-1 (2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amideYield 58.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-4bd1f3185be84872a4e733ec9d2b85c1
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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