Dimethyl Sulfoxide → N-[(5-Bromopyridin-3-yl)methyl]-10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244205
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[Br:37][C:38]1[CH:39]=[C:40]([CH2:44][NH2:45])[CH:41]=[N:42][CH:43]=1.C(N(CC)CC)C.CS(C)=O>C(#N)C>[Br:37][C:38]1[CH:39]=[C:40]([CH2:44][NH:45][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH3:34])=[CH:25][CH:26]=4)=[O:20])[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13]3)=[CH:7][CH:6]=2)=[O:4])[CH:41]=[N:42][CH:43]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneHCID 229922643-(Aminomethyl)-5-bromopyridine

Produkt 1

HCID 15953081N-[(5-Bromopyridin-3-yl)methyl]-10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone (0.288 g, 0.534 mmol), (5-bromopyridin-3-yl)methylamine of Step C (0.20 g, 1.07 mmol), triethylamine (0.043 g, 0.588 mmol), dimethylsulfoxide (0.190 mL, 2.67 mmol), and acetonitrile (5 mL) was heated for 17 hours at an oil bath temperature of 81° C. The solvent was removed under reduced pressure and the resulting residue taken up in dichloromethane. The organics were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a yellow solid. The solid was triturated with hexane, diethyl ether, and ethyl acetate, collected by filtration, and dried under reduced pressure to give the title compound (0.145 g) as an off white solid, m.p 180-184° C.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. washThe organics were washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure to a yellow solid
  5. customThe solid was triturated with hexane, diethyl ether, and ethyl acetate
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bae5c350b9c7477798dfe3902330a62c
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678787B2

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