Triethylamine → 4'-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

HRID 2091951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091951
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([NH:30][CH3:31])=[O:29])=[CH:24][CH:23]=2)=[C:16]([CH3:32])[CH:15]=1.C(N(CC)CC)C>ClCCCl.CC(O)(C)C.[Cl-].[Zn+2].[Cl-]>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([NH:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)=[C:16]([CH3:32])[CH:15]=2)[N:7]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 595867914'-Amino-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

Produkt 1

HCID 866477934'-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To the mixture of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (100 mg, 0.46 mmol) in 0.5 mL of DCE and 0.5 mL of t-BuOH is added zinc chloride (1.0 M in ether, 0.46 mL, 0.46 mmol), and stirred 30 min. 4′-amino-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide (111 mg, 0.414 mmol) and triethylamine (46 mg, 0.46 mmol) are added sequentially, and the reaction is stirred at room temperature overnight. The precipitate is filtered, washed by MeOH, and dried in vacuo to afford 4′-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide as a white solid; ESMS m/z 451.1 (M+H+).

Aufarbeitung

  1. stirringthe reaction is stirred at room temperature overnight
  2. filtrationThe precipitate is filtered
  3. washwashed by MeOH
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c0ed4d1ae9114672a198ece0ddd6b8c6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440681B2

Notizen zur Reaktion

Wird geladen…