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Triethylamine → 4-amino-5-cyano-N-(2,5-dimethoxybenzyl)-6-ethoxypyridine-2-carboxamide

HRID 1364537
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HRID 1364537 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:19]=1[CH2:20][NH2:21].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:21][CH2:20][C:19]2[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=2[O:17][CH3:16])=[O:15])[CH:3]=1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 186522,5-DimethoxybenzenemethanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

생성물 1

HCID 118464594-amino-5-cyano-N-(2,5-dimethoxybenzyl)-6-ethoxypyridine-2-carboxamide

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To 4-amino-5-cyano-6-ethoxy-pyridine-2-carboxylic acid (0.1 mmol) in DMF (0.1 mL) was added 2,5-dimethoxybenzylamine (0.2 mmol), Et3N (0.2 mmol), and TBTU (0.1 mmol) sequentially. The reaction mixture was stirred at ambient temperature for 16 hours and water was added. The precipitates were collected and purified by column chromatography to provide the titled compound. 1H NMR (400 MHZ, DMSO-d6) δ 8.81 (t, J=6.4 Hz, 1H), 7.31 (broad s, 2H), 7.07 (s, 1H), 6.92 (d, J=8.8 Hz, 1H), 6.79 (dd, J=2.8, 8.8 Hz, 1H), 6.72 (d, J=3.2 Hz, 1H), 4.49 (q, J=7.2 Hz, 2H), 4.42 (d, J=6.4 Hz, 2H), 3.79 (s, 3H), 3.65 (s, 3H), and 1.33 (t, J=7.2, 3H). MS (m/e) positive mode: 357 (M+H)+, 379 (M+Na)+; negative mode: 355 (M−H)−.

후처리

  1. customThe precipitates were collected
  2. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-e22981d8ebfa4c68916b5ae2728ae7cc
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888374B2

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