2,5-Dimethoxyphenylboronic acid → 4-amino-8-(2,5-dimethoxyphenyl)-N-ethylcinnoline-3-carboxamide

HRID 2375669

반응식

HRID 2375669 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[CH:25]=[C:20]([O:19][CH3:18])[CH:21]=[CH:22][C:23]=3[O:26][CH3:27])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]

참가 물질

3

반응물 2

HCID 27343422,5-Dimethoxyphenylboronic acidHCID 672286714-Amino-8-bromo-N-ethyl-cinnoline-3-carboxamide

생성물 1

HCID 236296624-amino-8-(2,5-dimethoxyphenyl)-N-ethylcinnoline-3-carboxamide수율 54%

실험 절차

The title compound was prepared from 4-amino-8-bromo-N-ethyl-cinnoline-3-carboxamide (100.0 mg, 0.339 mmol) and 2,5-dimethoxyphenyl boronic acid (123.3 mg, 0.678 mmol) according to Method A. The solid obtained after chromatography was washed with diethyl ether and dried overnight at 40° C. to afford the title compound as a fluffy white solid (64.4 mg, 54% yield). 1H NMR (300.132 MHz, CDCl3) δ 8.51 (bt, J=5.2 Hz, 1H), 7.86 (dd, J=7.5, 2.1 Hz, 1H), 7.76-7.68 (m, 2H), 6.97-6.91 (m, 3H), 3.79 (s, 3H), 3.64 (s, 3H), 3.52 (dq, J=5.7, 7.3 Hz, 2H), 1.26 (t, J=7.3 Hz, 3H). MS APCI, m/z=353 (M+H). HPLC 2.41 min.

후처리

  1. customThe solid obtained after chromatography
  2. washwas washed with diethyl ether
  3. customdried overnight at 40° C.

출처 및 근거

ORD 기록
ord-c6b9c8cb0a5d4910ab53fd5fdaec11cd
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465795B2

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