Dimethyl Sulfoxide → 10-{[(4-Bromophenyl)thio]acetyl}-N-(3,4-dichlorobenzyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639285
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:29])[CH2:20][S:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:36][NH2:37].CS(C)=O>C(#N)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([S:21][CH2:20][C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:37][CH2:36][C:35]4[CH:38]=[CH:39][C:40]([Cl:41])=[C:33]([Cl:32])[CH:34]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:29])=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 1608Benzenemethanamine, 3,4-dichloro-HCID 160393672,2,2-trichloro-1-[10-{[(4-bromophenyl)thio]acetyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl]-ethanone

Produkt 1

HCID 1603936810-{[(4-Bromophenyl)thio]acetyl}-N-(3,4-dichlorobenzyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To an 18×150 mm reaction vessel was added 2,2,2-trichloro-1-[10-{[(4-bromophenyl)thio]acetyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl]-ethanone of Example 80 (0.23 mmol), acetonitrile (2.5 mL), 3,4-dichlorobenzylamine (0.49 mmol), and dimethylsulfoxide (0.81 mmol). The stirred solution was heated to 85° C. for 20 hours. The solvent was evaporated and the residue was dissolved in 5 mL dichloromethane. The solution was washed twice with water, dried over anhydrous sodium sulfate, and evaporated. The crude product was purified using normal phase HPLC with a two phase solvent system (A=hexane, B=dichloromethane/methanol, 4:1) to give the title product, m.p. 150° C. MS [(+)ESI, m/z]: 614 [M+H]+ Anal. Calcd for C28H22BrCl2N3O2S: C, 54.65; H, 3.60; N, 6.83. Found: C, 54.68; H, 3.50; N, 6.73.

Aufarbeitung

  1. customTo an 18×150 mm reaction vessel
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 5 mL dichloromethane
  4. washThe solution was washed twice with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-41c5677bd2724e79a87922a092587653
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691848B2

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