Potassium Hydroxide → HCID 86758788, compound

HRID 1634213Notes

Reaction equation

HRID 1634213 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[C:4]([NH2:17])[N:3]=1.C1(C)C=C(C)C=C(C)C=1S([NH:29]O)(=O)=O.[Br:32][C:33]1[O:37][C:36]([CH:38]=O)=[CH:35][CH:34]=1.[OH-].[K+]>O1CCOCC1.CO>[NH2:17][C:4]1[N:3]2[N:29]=[C:38]([C:36]3[O:37][C:33]([Br:32])=[CH:34][CH:35]=3)[N:1]=[C:2]2[CH:7]=[C:6]([CH2:8][NH:9][C:10]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:11])[CH:5]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 6003285-Bromofuran-2-carbaldehydeHCID 11009332O-mesitylenesulfonylhydroxylamineHCID 86758787HCID 86758787, compound

Product 1

HCID 86758788HCID 86758788, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 39 mg (0.17 mmol) cyclopentanecarboxylic acid (2,6-diamino-pyridin-4-ylmethyl)-amide in 1.4 ml dioxane was added 40.2 mg (0.187 mmol, 1.1 eq.) o-mesitylenesulfonylhydroxylamine and after 2h 38.6 mg (0.221 mmol, 1.3 eq.) 5-bromo-2-furaldehyde. The mixture was heated to 100° C. for 2.5 h and afterwards 0.17 ml 1N KOH in MeOH was added. Opening of the reaction vessel and stirring of the mixture at room temperature for 16 h preceded the evaporation to dryness. The residue was taken up in 4.5 ml water and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried with MgSO4 and evaporated. Purification of the residue with column chromatography on silica eluting with yielded the 12 mg (21%) of the title compound.

Workup

  1. customthe evaporation to dryness
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. customevaporated
  5. customPurification of the residue with column chromatography on silica eluting

Sources & evidence

ORD record
ord-52d48d653c7f494c8dfdcf5982e9271d
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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