Potassium Carbonate → HCID 86672803, compound

HRID 1755133Notes

Reaction equation

HRID 1755133 reaction equation
[C:1]([O:5][C:6](=[O:41])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:39][CH2:38][C:21]3([N:25]=[C:24]([C:26]4[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([OH:36])[CH:27]=4)[NH:23][C:22]3=[O:37])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:9]([CH3:40])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:42]([O:46][C:47]([N:49]([CH3:72])[CH2:50][CH2:51][O:52][CH2:53][C:54]([F:71])([F:70])[C:55]([F:69])([F:68])[C:56]([F:67])([F:66])[CH2:57]OS(C(F)(F)F)(=O)=O)=[O:48])([CH3:45])([CH3:44])[CH3:43].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:41])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:19][CH2:20][C:21]3([N:25]=[C:24]([C:26]4[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[C:28]([O:36][CH2:57][C:56]([F:66])([F:67])[C:55]([F:68])([F:69])[C:54]([F:70])([F:71])[CH2:53][O:52][CH2:51][CH2:50][N:49]([C:47]([O:46][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:48])[CH3:72])[CH:27]=4)[NH:23][C:22]3=[O:37])[CH2:38][CH2:39]2)(=[O:16])=[O:17])=[C:9]([CH3:40])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66818415HCID 66818415, compoundHCID 86672804HCID 86672804, compound

Product 1

HCID 86672803HCID 86672803, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-{2-[2-(3-Hydroxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester (77.0 mg, 0.13 mmol) and trifluoro-methanesulfonic acid 5-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-2,2,3,3,4,4-hexafluoro-pentyl ester (58.0 mg, 0.13 mmol) were dissolved in DMF (1 ml). Potassium carbonate (53.8 mg, 0.39 mmol) was added and the mixture was stirred at 60° C. overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was then washed with saturated brine, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-{2-[2-(3-{5-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-2,2,3,3,4,4-hexafluoro-pentyloxy}-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester (57 mg, 46%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was then washed with saturated brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-94e503c8575f49f7a2bf1abb33225a29
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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