3,5-Dimethylpyrazole → HCID 178509134, compound

HRID 1349765Notes

Reaction equation

HRID 1349765 reaction equation
[NH2:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O.CC1C=[C:25](C)[NH:24]N=1.C([N:30](CC)CC)C>O.C(O)CCC>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[C:5]([C:3]4[NH:30][C:25]([NH2:24])=[N:1][N:2]=4)[CH:6]=3)[NH:10][N:9]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 8471TriethylamineHCID 22479863HCID 22479863, compound

Product 1

HCID 178509134HCID 178509134, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-amino[3-(4-fluorophenyl)(1H-indazol-5-yl)]carboxamide (440 mg, 1.6 mmol) and 3,5-dimethylpyrazole (321 mg, 1.6 mmol) in water (˜15 mL) was added triethylamine (0.21 mL, 1.6 mmol). The reaction was heated to reflux overnight. The solvent was removed and the crude reaction mixture was taken up in butanol with molecular sieves. The reaction was heated to reflux overnight. The molecular sieves were removed and the solution concentrated. The crude mixture was purified by preparative HPLC. The material was taken up in ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate, filtered and concentrated to yield the title compound (0.022 g, 4.6% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 12.0 (s, 1H), 8.5 (s, 1H), 8.0 (m, 3H), 7.7 (d, 1H), 7.4 (m, 2H), 6.1 (s, 2H), ES-MS (m/z) 295 [M+1]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe crude reaction mixture
  5. temperatureThe reaction was heated
  6. temperatureto reflux overnight
  7. customThe molecular sieves were removed
  8. concentrationthe solution concentrated
  9. customThe crude mixture was purified by preparative HPLC
  10. washwashed with aqueous sodium bicarbonate
  11. dry with materialThe organic layer was dried with magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-0a6c725fb7ed400f8f73cc1d6fbf1f73
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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