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Water → (R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 84838
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 84838
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([NH2:13])=[O:12])=[C:5]([F:18])[C:4]=1F)#[N:2].Cl.[NH2:21][C:22]1[S:26][N:25]=[C:24]([CH3:27])[CH:23]=1.[H-].[Na+].[OH2:30]>CS(C)=O.CCOC(C)=O>[NH2:13][C:11](=[O:12])[C@H:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]([NH2:2])=[O:30])=[C:4]([NH:21][C:22]2[S:26][N:25]=[C:24]([CH3:27])[CH:23]=2)[C:5]=1[F:18])[CH2:14][CH:15]([CH3:17])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 67508536(R)-2-(4-cyano-2,3-difluorophenylamino)-4-methylpentanamide

Produkt 1

HCID 57334186(R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-(4-cyano-2,3-difluorophenylamino)-4-methylpentanamide (113 mg, 0.423 mmol) and 5-amino-3-methylisothiazole hydrochloride (70 mg, 0.464 mmol) in DMSO (3 mL), NaH (60% in mineral oil, 100 mg, 2.50 mmol) was added. H2 gas evolved. The mixture was stirred at 130 C for 30 min. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. To a solution of the residue in EtOH (2 mL) and DMSO (0.5 mL), 1N aq. NaOH (0.5 mL) and H2O2 (50% aq., 0.5 mL) were added. After being stirred at room temperature for 30 min, the mixture was concentrated in vacuo. The residue was acidified with HOAc (0.5 mL), and then was purified by HPLC to give the titled compound (36 mg). MS 380.4 (M+H); UV 202.2, 280.5 nm

Aufarbeitung

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. additionTo a solution of the residue in EtOH (2 mL) and DMSO (0.5 mL), 1N aq. NaOH (0.5 mL) and H2O2 (50% aq., 0.5 mL) were added
  5. stirringAfter being stirred at room temperature for 30 min
  6. concentrationthe mixture was concentrated in vacuo
  7. customwas purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-594a53672d09489fbabb5ece7b02878f
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846928B2

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