1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-bromo-N-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 2284620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284620
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=2)[CH:7]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:41]=[C:42]([O:46][CH3:47])[C:43]=1[O:44][CH3:45])[NH2:40].CCN(C(C)C)C(C)C>C(#N)C.CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([NH:40][C:39]3[CH:41]=[C:42]([O:46][CH3:47])[C:43]([O:44][CH3:45])=[C:37]([O:36][CH3:35])[CH:38]=3)=[O:13])=[CH:9][N:10]=2)[CH:7]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 322853,4,5-TrimethoxyanilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 220319126-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Produkt 1

HCID 867155346-bromo-N-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

A stirring solution of 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (0.91 g, 3.7 mmol), EDCI (1.08 g, 5.6 mmol), HOBt (0.76 g, 5.6 mmol) and 3,4,5-trimethoxyaniline (0.76 g, 4.1 mmol) in acetonitrile/DMF (8/3 mL) under argon was added i-Pr2NEt (2.00 g, 2.6 ml), 15.4 mmol) drop wise for 5 min at room temperature. The resulting off-brown homogeneous reaction mixture was continued to stir at room temperature for 18 h. Subsequently, the heterogeneous reaction mixture was diluted with water and the solid was collected by filtration. The solid was suction dried on funnel to obtain 6-bromo-N-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamide (1.1 g) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.17 (s, 1H), 9.64 (s, 1H), 8.56 (d, J=1.1 Hz, 1H), 7.75 (d, J=9.7 Hz, 1H), 7.64 (dd, J=9.5, 1.9 Hz, 1H), 7.15 (s, 2H), 3.78 (s, 6H), 3.63 (s, 3H).

Aufarbeitung

  1. filtrationthe solid was collected by filtration
  2. customdried on funnel

Quellen und Nachweise

ORD-Eintrag
ord-b588745637ca447fb3cfd1d79a08672a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145433B2

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