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

HRID 2284620Notes

Reaction equation

HRID 2284620 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 867155346-bromo-N-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamideYield 73.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b588745637ca447fb3cfd1d79a08672a
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

Loading…