Potassium Carbonate → HCID 178454360, compound

HRID 82766Notes

Reaction equation

HRID 82766 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2F)/[N:7]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH2:31].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:12]2[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:13]=2[NH:31][NH:30][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:23])/[N:7]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70091tert-Butyl carbazateHCID 178441320HCID 178441320, compound

Product 1

HCID 178454360HCID 178454360, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 1A (203 mg, 0.47 mmol), tert-butyl hydrazinecarboxylate (187 mg, 1.42 mmol) and potassium carbonate (196 mg, 1.42 mmol) in dioxane (15 mL) was warmed to reflux for 24 hours. The mixture was concentrated under reduced pressure and extracted with ethyl acetate. The acetate extract was washed with water, brine, dried with MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography (SiO2) to afford 40 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.31-1.47 (m, 18 H), 1.64-2.04 (m, 4 H), 3.66 (t, J=7.1 Hz, 1 H), 3.75-3.89 (m, 1 H), 4.23-4.40 (m, 3 H), 6.12 (s, 1 H), 6.99 (d, J=9.1 Hz, 1 H), 7.36 (s, 1 H), 7.65 (dd, J=8.9, 1.8 Hz, 1 H), 8.43 (d, J=2.0 Hz, 1 H), 10.11 (s, 1 H). MS (DCI/NH3) m/z 543 (M+H)+.

Workup

  1. temperatureto reflux for 24 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. extractionThe acetate extract
  5. washwas washed with water, brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography (SiO2)

Sources & evidence

ORD record
ord-de944d58cf434169b7897071af5472b8
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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