Trifluoroacetic acid → (E)-3-(4-oxo-7-(2-(pyridin-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrile

HRID 1745678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1745678
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][C:9]=1[NH2:22])(C)(C)C.CC1(C)O[C:29]([C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)[C:34]#[N:35])=[CH:28][C:27](=[O:39])O1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:39]=[C:27]1[CH2:28][C:29]([C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)[C:34]#[N:35])=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:9]=2[NH:22]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 117363373-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrileHCID 69592755tert-Butyl {2-amino-4-[(pyridin-2-yl)ethynyl]phenyl}carbamate

Produkt 1

HCID 22224608(E)-3-(4-oxo-7-(2-(pyridin-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrileAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared from (2-amino-4-pyridin-2-ylethynyl-phenyl)-carbamic acid tert.-butyl ester (Example G19) (124 mg, 0.4 mmol) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example J4) (147 mg, 0.48 mmol) according to the general procedure K. The obtained material (199 mg) was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a yellow solid (124 mg).

Quellen und Nachweise

ORD-Eintrag
ord-1c1faca244ed4913bb7c3b2468917d88
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07018998B2

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