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

HRID 2284620ノート

反応式

HRID 2284620 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21891449acetonitrile N,N-dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b588745637ca447fb3cfd1d79a08672a
出典データセット
uspto-grants-2015_09
特許番号
US09145433B2

反応ノート

読み込み中…