1-Chloroethyl chloroformate → 4-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

HRID 489239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489239
ClC(OC(Cl)C)=O.C([N:15]1[CH2:34][C@@H:33]([C:35]2[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=2)[C@:17]2([N:21]([CH3:22])[C:20](=[O:23])[N:19]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)[C:18]2=[O:32])[CH2:16]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:31][C:26]1[CH:25]=[C:24]([N:19]2[C:18](=[O:32])[C@@:17]3([C@H:33]([C:35]4[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=4)[CH2:34][NH:15][CH2:16]3)[N:21]([CH3:22])[C:20]2=[O:23])[CH:29]=[C:28]([Cl:30])[CH:27]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 119945114-[(5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

Produkt 1

HCID 119947544-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrileAusbeute 116,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Chloroethyl chloroformate (4.4 ml, 40.3 mmol) was added to a cooled (5° C.) solution of Example 14 (5.1 g, 10.1 mmol) in DCM (250 ml). After 1 h at 5° C., the reaction mixture was stirred at RT for 20 h. The solution was concentrated to dryness and then refluxed in MeOH (350 ml) for 3 h. After concentration in vacuo, the oily residue was triturated in Et2O to give the hydrochloride of the desired compound (4.9 g). After basification, the product was chromatographed over silica gel (DCM/MeOH 90/10) to yield the above-titled compound (3.35 g) as an amorphous solid. 1H NMR (CDCl3): 7.64 (2H, d, J=8.4 Hz), 7.25-7.32 (3H, m), 6.72 (2H, d, J=2 Hz), 3.6-3.75 (2H, m), 3.35-3.55 (3H, m), 3.20 (3H, s), 2.16 (1H, br s).

Aufarbeitung

  1. concentrationThe solution was concentrated to dryness
  2. temperaturerefluxed in MeOH (350 ml) for 3 h
  3. concentrationAfter concentration in vacuo
  4. customthe oily residue was triturated in Et2O

Quellen und Nachweise

ORD-Eintrag
ord-9e6ffcb958b54bd9bfc1c2e073ca539d
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977267B2

Notizen zur Reaktion

Wird geladen…