Cesium carbonate → 4-(3-(1H-imidazol-1-yl)benzylamino)-6-(4-(dimethylcarbamoyl)phenylamino)nicotinamide

HRID 513282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513282
[N:1]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][NH:10][C:11]2[C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:1]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][NH:10][C:11]2[C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=[C:13]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([C:29](=[O:30])[N:31]([CH3:32])[CH3:33])=[CH:34][CH:35]=3)[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 2355274-Amino-N,N-dimethylbenzamideHCID 634876Binap, (A+-)-HCID 866645474-(3-(1H-imidazol-1-yl)benzylamino)-6-chloronicotinamide

Produkt 1

HCID 569684754-(3-(1H-imidazol-1-yl)benzylamino)-6-(4-(dimethylcarbamoyl)phenylamino)nicotinamideAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of 4-(3-(1H-imidazol-1-yl)benzylamino)-6-chloronicotinamide (56 mg, 0.170 mmol), 4-amino-N,N-dimethylbenzamide (42 mg, 0.256 mmol), Cs2CO3 (110 mg, 0.337 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 120 C for 3 h. The mixture was concentrated in vacuo, the residue was purified by HPLC to give the titled compound (7 mg). MS 456.3 (M+H); UV 257.8 nm; t 0.344 min.

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-605737e9bf7a4f22bc07d5b40639400e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102625B2

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