Sodium Hydroxide → 3-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

HRID 251342

Reaktionsgleichung

Reaktionsgleichung von HRID 251342
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[C:15]1([CH3:25])[CH:20]=[CH:19]C(S(O)(=O)=O)=[CH:17][CH:16]=1.N[CH:27]([C:30]#[N:31])[C:28]#[N:29].[C:32]([O-:35])(=O)[CH3:33].[Na+].[OH-].[Na+]>C(OCC)(OCC)OCC.O>[NH2:31][C:30]1[N:1]([C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=2[CH3:14])[C:5]([NH:7][CH:8]2[CH2:9][CH2:10]2)=[O:6])[N:29]=[CH:28][C:27]=1[C:32](=[O:35])[C:33]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 563049Aminomalononitrile p-toluenesulphonateHCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 111647033-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31214Ethyl orthoformateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3-amino-N-cyclopropyl-4-methyl-benzamide 1 (380 mg, 2.0 mmol) in 2.0 mL of triethyl orthoformate was stirred at 120° C. in microwave for 20 minutes. The solvent was removed under reduced pressure. The residue was dissolved in 5 mL of acetic acid and then was added aminomalononitrile p-toluenesulfonate (506 mg, 2.0 mmol) and sodium acetate (164 mg, 2.0 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with 20 mL of water and then its pH was adjusted to 8.0 by aqueous NaOH. The resulting mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo evaporated. The residue was purified by silica gel column chromatography (10/1, methylene chloride:methanol) to give 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide 3 as a colorless solid (170 mg, 30%). HPLC (4 minute gradient) tR=1.39 min; MS m/z 282 [M+H].

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 5 mL of acetic acid
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. extractionThe resulting mixture was extracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customevaporated
  10. customThe residue was purified by silica gel column chromatography (10/1, methylene chloride:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-58d9bc116e3d41c3b7a02aebc0b2eda8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863314B2

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