Triethylamine → HCID 67059707, compound

HRID 1807735Notes

Reaction equation

HRID 1807735 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:21]2[CH2:22][CH2:23][N:18]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:19][CH2:20]2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 67059707HCID 67059707, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-aminonicotinic acid (1 g, 7.24 mmol) in dimethylformamide (50 mL) was added 1-benzylpiperazine (1.258 mL, 1.276 g, 7.24 mmol), triethylamine (2.018 mL, 1.465 g, 14.48 mmol), 1-hydroxybenzotriazole hydrate (1.109 g, 7.24 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.388 g, 7.24 mmol). After being stirred overnight at room temperature the reaction mixture was concentrated under vacuum. Purification by silica chromatography (eluting with 5% methanol/dichloromethane) gave the title compound (1.8 g).

Workup

  1. concentrationwas concentrated under vacuum
  2. customPurification
  3. washby silica chromatography (eluting with 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-074ab54227be41188db70e47725d14a5
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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