Hydrogen Peroxide → 4-((1R,2S)-2-aminocyclohexylamino)-2-(1-methyl-1H-pyrazol-4-ylamino)benzamide

HRID 2201034

Reaktionsgleichung

Reaktionsgleichung von HRID 2201034
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16]C(=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:24][C:25]1[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=1)#[N:2].C([O-])([O-])=[O:32].[K+].[K+].OO.O>CS(C)=O.CCOC(C)=O>[NH2:16][C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]([NH2:2])=[O:32])=[C:4]([NH:24][C:25]2[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=2)[CH:5]=1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 68077202tert-butyl (1S,2R)-2-(4-cyano-3-(1-methyl-1H-pyrazol-4-ylamino)phenylamino)cyclohexylcarbamate

Produkt 1

HCID 573343354-((1R,2S)-2-aminocyclohexylamino)-2-(1-methyl-1H-pyrazol-4-ylamino)benzamideAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (1S,2R)-2-(4-cyano-3-(1-methyl-1H-pyrazol-4-ylamino)phenylamino)cyclohexylcarbamate (50 mg, 0.12 mmol) in DMSO (1 mL), K2CO3 (100 mg, 0.724 mmol) and H2O2 (50% aq., 0.800 mL) were added. The mixture was stirred at 100 C for 10 min. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was dissolved in TFA (1 mL). After 10 min of standing, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (31 mg). MS 329.4 (M+H); UV 205.3, 258.4, 280.5, 327.9 nm

Aufarbeitung

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in TFA (1 mL)
  5. waitAfter 10 min of standing
  6. customTFA was removed in vacuo
  7. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5ee65d6d35a948b2a7ca22b8eef6caca
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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