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

HRID 1364537Notes

Reaction equation

HRID 1364537 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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)−.

Workup

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

Sources & evidence

ORD record
ord-e22981d8ebfa4c68916b5ae2728ae7cc
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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