Potassium Carbonate → HCID 58333380, compound

HRID 2066868Notes

Reaction equation

HRID 2066868 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:26]([F:27])=[CH:25][C:24]([CH2:28][OH:29])=[C:23](Cl)[N:22]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:31]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:26]([F:27])=[CH:25][C:24]([CH2:28][OH:29])=[C:23]([CH3:31])[N:22]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 866550124-(6'-Chloro-3'-fluoro-5'-hydroxymethyl-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 58333380HCID 58333380, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

55b (30 mg, 0.068 mmol), trimethylboroxine (25 mg, 0.2 mmol) and potassium carbonate (50 mg, 0.36 mmol) were combined in 0.5 mL of dioxane and heated at 100° C. for 20 h. The mixture was cooled, concentrated under a stream of nitrogen, diluted with water (2 mL) and extracted with ethyl acetate (2×2 mL). The combined extracts were dried under a stream of nitrogen and the residue was purified by preparative HPLC to afford 55-1 as a colorless oil: LC-MS 423.1 (MH+), tR=5.95 (Method 2). EC50: 206 nM.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under a stream of nitrogen
  3. additiondiluted with water (2 mL)
  4. extractionextracted with ethyl acetate (2×2 mL)
  5. customThe combined extracts were dried under a stream of nitrogen
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b764c3138bb1430da832dfedb3978457
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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