Potassium Hydroxide → HCID 58074569, compound

HRID 1848363Notes

Reaction equation

HRID 1848363 reaction equation
[NH2:1][N+:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Br:10])[C:3]=1[NH2:11].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[CH2:25]([O:27][C:28]([C:30]1([CH:33]=O)[CH2:32][CH2:31]1)=[O:29])[CH3:26].[OH-].[K+]>O1CCOCC1.CO>[CH2:25]([O:27][C:28]([C:30]1([C:33]2[N:11]=[C:3]3[C:4]([Br:10])=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[N:2]3[N:1]=2)[CH2:32][CH2:31]1)=[O:29])[CH3:26]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 86655558HCID 86655558, compound2×

Product 1

HCID 58074569HCID 58074569, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

1.0 g (2.6 mmol) of crude 2,4,6-Trimethyl-benzenesulfonate 1,2-diamino-3-bromo-6-methoxy-pyridinium (see preparation of compound 311) was dissolved in dioxane (8.5 mL), under argon, and treated with 1-formyl-cyclopropanecarboxylic acid ethyl ester (0.56 g, 3.9 mmol) and heated to 90° C. for 22 hours. The brown solution was cooled to rt and treated with 1N KOH in MeOH (2.6 mL) and left at rt for 6 hours. The solvent was evaporated in vacuo and a NaCl solution was added to the product as well as aq. NaHCO3. The product was extracted with DCM (×3) and the combined organic phases was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using DCM:EtOAc 96:4->85:15 as eluent. The title compound was obtained as a colourless solid (0.22 g).

Workup

  1. temperatureThe brown solution was cooled to rt
  2. customThe solvent was evaporated in vacuo
  3. additiona NaCl solution was added to the product as well as aq. NaHCO3
  4. extractionThe product was extracted with DCM (×3)
  5. dry with materialthe combined organic phases was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-b46a2a0d6d754695b9909070247acbb6
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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