Acetonitrile → 2-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide

HRID 2387216

Reaktionsgleichung

Reaktionsgleichung von HRID 2387216
[NH2:1][C:2]1[N:13]=[CH:12][C:11](Br)=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[CH:15]1([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=2)(=[O:21])=[O:20])[CH2:17][CH2:16]1.C(Cl)Cl.CC#N>C([O-])([O-])=O.[Na+].[Na+].COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:13]=[CH:12][C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([S:19](=[O:20])(=[O:21])[NH:18][CH:15]3[CH2:16][CH2:17]3)[CH:23]=2)=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

Komponenten

9

Edukt 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 44119335(3-(N-Cyclopropylsulfamoyl)phenyl)boronic acidHCID 596997242-amino-5-bromo-N-methoxy-N-methylnicotinamide

Produkt 1

HCID 866345442-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

A suspension of 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide (0.2 g, 0.77 mmol), N-cyclopropyl 3-boronobenzenesulfonamide (0.2 g, 0.84 mmol), Pd(dppf)Cl2.DCM (0.063 g, 0.077 mmol) in 2M Na2CO3 (1 ml) and DME (3 ml) is heated at reflux for 1 hour. The crude reaction mixture is subjected to column chromatography (Isolute™ C18, 0-100% MeCN in water −0.1% TFA). All the acetonitrile is removed in vacuo, and the aqueous solution remaining is adjusted to basic pH using NaHCO3. The product is extracted into DCM, and dried (MgSO4). Concentration and drying in vacuo at 40° C. yields the title compound. [M+H]+ 726

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. customThe crude reaction mixture
  3. customAll the acetonitrile is removed in vacuo
  4. extractionThe product is extracted into DCM
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customdrying in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-0f769ef43d8646fbb8191300db62f2a9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268834B2

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