m-Tolyl isocyanate → N-[(3RS)-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea

HRID 963471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963471
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:3]1=[O:26].[C:27]1([CH3:36])[CH:32]=[CH:31][CH:30]=[C:29]([N:33]=[C:34]=[O:35])[CH:28]=1>ClCCl>[CH2:24]([O:23][C:21]([CH2:20][N:4]1[C:5]2[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=2[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[N:8][CH:2]([NH:1][C:34]([NH:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([CH3:36])[CH:28]=2)=[O:35])[C:3]1=[O:26])=[O:22])[CH3:25]

Komponenten

4

Edukt 2

HCID 69303m-Tolyl isocyanateHCID 10066773(3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Produkt 1

HCID 19081146N-[(3RS)-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)ureaAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3RS)-3-amino-2,3-dihydro-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (1.972 g) in dichloromethane (15 ml) was added dropwise a solution of m-tolyl isocyanate (0.884 g) in dichlromethane (5 ml) under stirring. After completion of the addition, the mixture was stirred for 4 hours at ambient temperature. The resultant white precipitates were collected by suction to give N-[(3RS)-2,3-dihydro-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea as a colorless crystalline solid (1.533 g). The filtrate was concentrated in vacuo. The residue was treated with chloroform and isopropyl ether to recover the desired compound (0.897 g).

Aufarbeitung

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 4 hours at ambient temperature
  3. customThe resultant white precipitates
  4. customwere collected by suction

Quellen und Nachweise

ORD-Eintrag
ord-418db77462894ee6b997e879daddf754
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763437

Notizen zur Reaktion

Wird geladen…