Lawesson's reagent → HCID 11305607, compound

HRID 1271072Notes

Reaction equation

HRID 1271072 reaction equation
COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[Cl:23][C:24]1[CH:54]=[CH:53][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([C:38](=O)[C:39]([NH:41][C:42]3[CH:43]=[C:44]4[C:49](=[CH:50][CH:51]=3)[N:48]=[CH:47][CH:46]=[CH:45]4)=[O:40])=[CH:30]2)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:54]=[CH:53][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([C:38](=[S:10])[C:39]([NH:41][C:42]3[CH:43]=[C:44]4[C:49](=[CH:50][CH:51]=3)[N:48]=[CH:47][CH:46]=[CH:45]4)=[O:40])=[CH:30]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10203597Entasobulin

Product 1

HCID 11305607HCID 11305607, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

3.68 g (9.1 mMol) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide are added, under nitrogen, to a suspension of 4.00 g (9.1 mMol) of 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-quinolin-6-ylacetamide in 200 ml of toluene, after which the mixture is heated at 75° C. for 3 h. The residue which has formed is filtered off in the hot from the reaction solution and subsequently washed with 100 ml of methylene chloride. The filtrate is concentrated in vacuo and the residue is chromatographed on flash silica gel (eluent: methylene chloride/methanol 99:1). The product fractions are filtered on flash silica gel (eluent: n-heptane/ethyl acetate 1:1) after the solvent has been removed once more.

Workup

  1. customThe residue which has formed
  2. filtrationis filtered off in the hot from the reaction solution
  3. washsubsequently washed with 100 ml of methylene chloride
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is chromatographed on flash silica gel (eluent: methylene chloride/methanol 99:1)
  6. filtrationThe product fractions are filtered on flash silica gel (eluent: n-heptane/ethyl acetate 1:1) after the solvent
  7. customhas been removed once more

Sources & evidence

ORD record
ord-1335eade7bc24499b9a2e5f1e4a479d7
Source dataset
uspto-grants-2007_04
Patent number
US07205299B2

Reaction notes

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