1,2-Dichloroethane → 1,3-Dihydro-5-phenyl-3(RS)-(3-trifluoromethylthiobenzoylamino)-2H-1,4-benzodiazepin-2-one

HRID 620579

Reaktionsgleichung

Reaktionsgleichung von HRID 620579
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](O)=[S:26].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[C:9]1([C:7]2[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3](=[O:19])[CH:2]([NH:1][C:25](=[S:26])[C:24]3[CH:28]=[CH:29][CH:30]=[C:22]([C:21]([F:20])([F:31])[F:32])[CH:23]=3)[N:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-oneHCID 178526136HCID 178526136, Verbindung

Produkt 1

HCID 200632131,3-Dihydro-5-phenyl-3(RS)-(3-trifluoromethylthiobenzoylamino)-2H-1,4-benzodiazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3(RS)-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (80.0 mg, 0.318 mmole), 3-trifluoromethylthiobenzoic acid (70.7 mg, 0.318 mmole), HBT (43.0 mg, 0.318 mmole) and EDC(61.0 mg, 0.318 mmole) were combined in dry DMF (2 ml) and stirred at room temperature. The pH of the mixture was adjusted to 9.0-9.5 with triethylamine (64.4 mg, 0.636 mmole) and the mixture stirred for 10 minutes. The DMF was removed in vacuo, and the residue was treated with 10% citric acid and extracted with EtOAc. The combined organic fractions were washed with sodium carbonate solution, dried over Na2SO4, filtered, and evaporated to dryness in vacuo. The residue was crystallized from EtOAc to give the title compound which was dried in vacuo at 100° C.: (m.p. 230°-232° C.).

Aufarbeitung

  1. stirringthe mixture stirred for 10 minutes
  2. customThe DMF was removed in vacuo
  3. additionthe residue was treated with 10% citric acid
  4. extractionextracted with EtOAc
  5. washThe combined organic fractions were washed with sodium carbonate solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-a84dfa094c974200a6e96025dbe3a669
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04820834

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