Hydrochloric Acid → aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone

HRID 1243826Notes

Reaction equation

HRID 1243826 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][C:10]=2[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:8]=1)=[O:6].[H-].[Na+].O.Cl>CN(C)C=O>[N:4]1([C:5]([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][C:10]=3[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 865940046,6-diphenyl-1 (2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amide

Product 1

HCID 21928926aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanoneYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 0.2 g of 6,6-diphenyl-1 (2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole-3-carboxylic acid (2-chloroethyl)amide in 7 cm3 of dimethylformamide is added dropwise to a suspension of 0.023 g of sodium hydride (at 60% in oil) in 3 cm3 of dimethylformamide cooled to a temperature in the region of 5° C. The reaction mixture is stirred for two hours at a temperature in the region of 20° C. The solution obtained is poured into a mixture of 30 cm3 of water and 0.3 cm3 of aqueous 1N hydrochloric acid solution while maintaining the temperature in the region of 5° C., and the mixture is extracted with three times 30 cm3 of ethyl acetate. The combined organic phases are washed with three times 30 cm3 of water and 30 cm3 of saturated aqueous sodium chloride solution, 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 (70/30 by volume)], 0.078 g of aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone is thus obtained in the form of a resin, the characteristics of which are as follows:

Workup

  1. customThe solution obtained
  2. temperaturewhile maintaining the temperature in the region of 5° C.
  3. extractionthe mixture is extracted with three times 30 cm3 of ethyl acetate
  4. washThe combined organic phases are washed with three times 30 cm3 of water and 30 cm3 of saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-da1275d6e30245ef8d2cba3fbd433bbb
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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