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

HRID 2284620노트

반응식

HRID 2284620 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 21891449acetonitrile N,N-dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b588745637ca447fb3cfd1d79a08672a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145433B2

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