Potassium Carbonate → (R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide

HRID 2201039

Reaktionsgleichung

Reaktionsgleichung von HRID 2201039
Br[C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH3:15])[C:12]([NH2:14])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[NH2:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[CH:19]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:10][C@H:11]([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:3][C:2]=1[NH:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[CH:19]=1)#[N:9]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 67509792(R)-2-(3-bromo-4-cyanophenylamino)propanamide

Produkt 1

HCID 67510271(R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamideAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)propanamide (185 mg, 0.690 mmol), 5-amino-3-methylisothiazole hydrochloride (133 mg, 0.883 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (30 mg, 0.13 mmol) and K2CO3 (300 mg, 2.17 mmol) in dioxane (4 mL) was degassed with Ar, then was stirred at 120 C for 18 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give ((R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (127 mg).

Aufarbeitung

  1. customwas degassed with Ar
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8377f8e118fe41fca002784f72d02aff
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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