Triethylamine → HCID 59346927, compound

HRID 20549Notes

Reaction equation

HRID 20549 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][O:26][CH3:27])[CH:22]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:9]=1)=[O:6].C(N([CH2:34][CH3:35])CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:16]([O:15][C:13]([C:35]1[CH:34]=[CH:21][C:22]([O:1][C:2]2[CH:3]=[C:4]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][O:26][CH3:27])[CH:22]=2)[C:5]([NH:7][C:8]2[CH:12]=[CH:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:9]=2)=[O:6])=[CH:2][CH:3]=1)=[O:14])[CH3:17]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59127185tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 59346927HCID 59346927, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (391 mg, 1 mmol), ethyl-4-boronic acid benzoate (388 mg, 2.0 equiv), copper (II) acetate (363 mg, 2.0 equiv) and triethylamine (0.7 mL; 5.0 equiv) were suspended in dry DCM over freshly activated powdered 4A molecular sieves (ca. 1 g) for 7 hours under an ambient atmosphere. Reaction mixture filtered through diatomaceous earth was washed with DCM (×3). Filtrate concentrated in vacuo, taken up in ethyl acetate and washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine and dried (MgSO4). Filtered, filtrate concentrated in vacuo and chromatographed (0-50% ethyl acetate/isohexane) to give a brown oil (210 mg, 39%).

Workup

  1. customfor 7 hours
  2. customReaction mixture
  3. filtrationfiltered through diatomaceous earth
  4. washwas washed with DCM (×3)
  5. concentrationFiltrate concentrated in vacuo
  6. washwashed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltered
  9. concentrationfiltrate concentrated in vacuo
  10. customchromatographed (0-50% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-4c466e908bf046fc954dac86ac97a6e8
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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