Water → (R)-2-(3-bromo-4-cyanophenylamino)-3-(1H-indol-3-yl)propanamide

HRID 84878

Reaktionsgleichung

Reaktionsgleichung von HRID 84878
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C@H:12]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:13]([NH2:15])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:9]=[C:8]([NH:11][C@H:12]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:13]([NH2:15])=[O:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 688582D-tryptophanamide

Produkt 1

HCID 67514877(R)-2-(3-bromo-4-cyanophenylamino)-3-(1H-indol-3-yl)propanamideAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-4-fluorobenzonitrile (160 mg, 0.800 mmol), (R)-2-amino-3-(1H-indol-3-yl)propanamide (164 mg, 0.807 mmol) and DIEA (0.300 mL, 1.72 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-80% EtOAc in hexane to give (R)-2-(3-bromo-4-cyanophenylamino)-3-(1H-indol-3-yl)propanamide (96 mg)

Aufarbeitung

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column, which
  5. washwas eluted with 0-80% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f6dd40fcc41b4bd491314c2b0ffc951d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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