Triethylamine → 2-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinamide

HRID 353229Notes

Reaction equation

HRID 353229 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:8]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH2:23][CH3:24])[CH:17]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O[N:26]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[Cl-].[NH4+].C(N(CC)CC)C>CN(C)C=O.O>[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:8]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH2:23][CH3:24])[CH:17]=2)=[CH:7][C:3]=1[C:4]([NH2:26])=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 129921372-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinic acid

Product 1

HCID 129921382-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinamideYield 45.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinic acid (20 mg, 61.5 μmol), 1-hydroxybenzotriazole (28 mg, 183 μmol), 3-(3′-dimethylaminopropyl)-1-ethyl carbodiimide (29 mg, 187 μmol), ammonium chloride (16 mg, 299 μmol), and a suspension of triethylamine (43 μL, 309 μmol) in N,N-dimethylformamide (1.0 mL) was stirred at room temperature for 18 hours. After diluting the reaction solution with water, the resulting solid was collected by filtration and washed with water, to give the title compound (9 mg, 45%) as a pale yellow solid.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-69ffcc4703ae41d09089501610369c9a
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

Loading…