Diisopropylethylamine → N-tert-Butyl-3-((4-(3-fluoro-4-(3-(5-(trifluoromethyl)pyridin-2-yl)ureido)benzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878335
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.C(N(C(C)C)C(C)C)C.[C:21](=O)(OC(Cl)(Cl)Cl)[O:22]C(Cl)(Cl)Cl.[NH2:33][C:34]1[CH:61]=[CH:60][C:37]([C:38]([N:40]2[CH2:45][CH2:44][N:43]([CH2:46][C:47]3[CH:48]=[C:49]([CH:57]=[CH:58][CH:59]=3)[C:50]([NH:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:42][CH2:41]2)=[O:39])=[CH:36][C:35]=1[F:62]>ClCCl>[C:53]([NH:52][C:50](=[O:51])[C:49]1[CH:57]=[CH:58][CH:59]=[C:47]([CH2:46][N:43]2[CH2:44][CH2:45][N:40]([C:38](=[O:39])[C:37]3[CH:60]=[CH:61][C:34]([NH:33][C:21]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]=4)=[O:22])=[C:35]([F:62])[CH:36]=3)[CH2:41][CH2:42]2)[CH:48]=1)([CH3:56])([CH3:55])[CH3:54]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 668785283-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Produkt 1

HCID 57917679N-tert-Butyl-3-((4-(3-fluoro-4-(3-(5-(trifluoromethyl)pyridin-2-yl)ureido)benzoyl)piperazin-1-yl)methyl)benzamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-(Trifluoromethyl)pyridin-2-amine (0.485 mmol, 0.079 g) and N-ethyl-N-isopropylpropan-2-amine (0.727 mmol, 0.120 mL, 0.094 g) were added to a stirred solution of bis(trichloromethyl) carbonate (0.160 mmol, 0.047 g) in dichloromethane (10 mL). The reaction was stirred for 3 hours at room temperature. 3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.242 mmol, 0.1 g) was added and the reaction stirred for 30 minutes. The reaction was heated in the microwave at 120° C. for 10 minutes. The reaction was concentrated under vacuum and purified by acidic reverse phase HPLC to afford the title compound (50 mg).

Aufarbeitung

  1. stirringthe reaction stirred for 30 minutes
  2. temperatureThe reaction was heated in the microwave at 120° C. for 10 minutes
  3. concentrationThe reaction was concentrated under vacuum
  4. custompurified by acidic reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-38fdedd871d9409ab6eebf55c88418a9
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314091B2

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