Tetrabutylammonium methoxide solution, 20% in methanol → (S)-5-acetyl-N-(1-(3-(4-cyano-3-methoxyphenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide

HRID 872650Notes

Reaction equation

HRID 872650 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:11][C@@H:12]([CH3:30])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([N+]([O-])=O)[CH:20]=3)=[N:15]2)=[O:10])[CH:5]=1)(=[O:3])[CH3:2].[CH3:31][O-:32].C([N+](CCCC)(CCCC)CCCC)CCC>CO>[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:11][C@@H:12]([CH3:30])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([O:32][CH3:31])[CH:20]=3)=[N:15]2)=[O:10])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11346348Tetrabutylammonium methoxide solution, 20% in methanol2×HCID 178466826HCID 178466826, compound

Product 1

HCID 178487550(S)-5-acetyl-N-(1-(3-(4-cyano-3-methoxyphenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamideYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(S)-5-acetyl-N-(1-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide (0.27 g, 0.663 mmol) was added to a flask and flushed with nitrogen. Dry THF was added and tetrabutylammonium methoxide solution in methanol (1.219 ml, 0.729 mmol) was added dropwise through a septum. During the reaction 1.754 ml of tetrabutylammonium methoxide solution in methanol was added and after reacting for 6 days the reaction was stopped. The crude product was evaporated and dissolved in DCM. The mixture was washed with water, dried and evaporated. Evaporation residue was dissolved in 20% methanol/DCM-solvent and filtered through silica wetted with the same solvent. The product was triturated using a small amount of DCM. Yield 5.00%. 1H-NMR (400 MHz; DMSO-d6): δ 1.16 (d, 3H), 2.5 (s, 3H), 3.94 (s, 3H), 4.31 (s, 2H), 4.40-4.50 (m, 1H), 6.88 (d, 1H), 7.31 (s, 1H), 7.46-7.54 (m, 2H), 7.71 (d, 1H), 7.80 (d, 1H), 8.49 (s, 1H), 14.12 (s, 1H).

Workup

  1. customflushed with nitrogen
  2. additionDry THF was added
  3. additionwas added
  4. customThe crude product was evaporated
  5. dissolutiondissolved in DCM
  6. washThe mixture was washed with water
  7. customdried
  8. customevaporated
  9. customEvaporation residue
  10. dissolutionwas dissolved in 20% methanol/DCM-solvent
  11. filtrationfiltered through silica
  12. customThe product was triturated

Sources & evidence

ORD record
ord-b27c97bb655c44dea373696b35c20c2c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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