Triethylamine → 1-[(e)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one

HRID 1867418Notizen

Reaktionsgleichung

Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][N:12]2[C:18](=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][C:31]=1[F:32])/[CH:24]=[CH:25]/[C:26](O)=[O:27].CCN(CC)CC.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23](/[CH:24]=[CH:25]/[C:26]([N:15]2[CH2:16][CH2:17][C:18](=[O:19])[N:12]([CH2:11][CH2:10][CH2:9][N:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]3)[CH2:13][CH2:14]2)=[O:27])[CH:29]=[CH:30][C:31]=1[F:32]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A suspension of 0.099 g (0.32 mmol) 4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one-dihydrochloride (intermediate 4B) and 0.077 g (0.38 mmol) of (E)-3-chloro-4-fluorocinnamic acid in 3 ml of CH2Cl2 was treated with 0.09 ml (0.64 mmol) of Et3N at RT, cooled (0° C.) and treated with a 0.085 g (0.41 mmol) of N,N′-dicyclohexylcarbodiimide. The reaction was warmed up over night to RT, then partitioned between EtOAc (×3)/saturated NaHCO3. The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to give after purification on catridges, Si-Amine, 70 ml, 20 g (EtOAc/n-heptane 9:1) 0.075 g (64%) of the title compound as a white solid. MS: 422.1 (MH+, Cl).

Aufarbeitung

temperatureThe reaction was warmed up over night to RT
custompartitioned between EtOAc (×3)/saturated NaHCO3
washThe organic phases were washed with aqueous 10% NaCl
dry with materialdried over Na2SO4
customevaporated
customto give
customafter purification on catridges, Si-Amine, 70 ml, 20 g (EtOAc/n-heptane 9:1) 0.075 g (64%) of the title compound as a white solid

Quellen und Nachweise

ORD-Eintrag: ord-54046ff0ee5c4ecc8796c7eedb7a2e95
Quelldatensatz: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07632829B2

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