Acetone → HCID 21200530, compound

HRID 1585740Notes

Reaction equation

[CH3:1][N:2]([CH3:4])[NH2:3].C([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])C.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C[C:24](C)=[O:25]>C(Cl)Cl>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[CH3:1][N:2]([CH3:4])[NH:3][C:24]([C:22]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:8][NH:7][CH2:10][CH2:11]1)=[O:25]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 7.15 g of the compound obtained in step B of PREPARATION 1.28 in 60 ml of DCM is cooled to 5° C., a solution of 1.44 g of 1,1-dimethylhydrazine and 4.04 g of triethylamine in 20 ml of DCM is added dropwise and the reaction mixture is left stirring overnight at RT. It is concentrated under vacuum, the residue is taken up with water, the product is extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The product obtained is dissolved in 100 ml of acetone, a solution of 3.59 g of p-toluenesulphonic acid in 10 ml of acetone is added rapidly and the mixture is concentrated under vacuum. The residue is taken up in an ether/DCM mixture and the precipitate formed is drained. 9.65 g of the expected product are obtained.

Workup

waitthe reaction mixture is left
concentrationIt is concentrated under vacuum
extractionthe product is extracted with AcOEt
washthe organic phase is washed with saturated NaCl solution
dry with materialdried over Na2SO4
customthe solvent is evaporated off under vacuum
customThe product obtained
concentrationthe mixture is concentrated under vacuum
customthe precipitate formed

Sources & evidence

ORD record: ord-b3427359afb34e2e97dceea391a034fd
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939411

Reaction notes

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