Triethylamine → HCID 178425200, compound

HRID 1501225Notes

Reaction equation

HRID 1501225 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[CH:15]=[CH:14][C:10](C(O)=O)=[CH:9][CH:8]=1)#[N:2].Cl.C(N=C=NCCC[N:28]([CH3:30])C)C.[OH:31]N1C2C=CC=CC=2N=N1.C(N(CC)CC)C.N[CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>ClCCl>[C:30]([C:14]1[CH:15]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:6][C:5]1[CH:4]=[C:3]([CH:18]=[CH:17][CH:16]=1)[C:1]([NH:2][CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56])=[O:31])#[N:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25271922HCID 25271922, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425200HCID 178425200, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-cyanophenoxy)benzoic acid (40 mg, 0.17 mmol) in dichloromethane (20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (48 mg, 0.25 mmol), N-hydroxy benzotriazole (34 mg, 0.25 mmol) and triethylamine (34 mg, 0.33 mmol), stirred for 30 min. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (26 mg, 0.17 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (50 mL), dried over sodium sulfate, concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 3-(3-cyanophenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (21 mg, 58%)

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-cbe9a491638546d385e509cc854c5ad8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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