Triethylamine → HCID 178492316, compound

HRID 1501220Notes

Reaction equation

HRID 1501220 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:46][CH2:47][C:48]1[C:49]([OH:57])=[N:50][C:51]([CH3:56])=[CH:52][C:53]=1[O:54][CH3:55]>ClCCl.O>[OH:57][C:49]1[C:48]([CH2:47][NH:46][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:53]([O:54][CH3:55])[CH:52]=[C:51]([CH3:56])[N:50]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178492315HCID 178492315, compound

Product 1

HCID 178492316HCID 178492316, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenoxybenzoic acid (60 mg, 0.28 mmol) in dichloromethane (15 mL) were added 1-Hydroxybenzotriazole (49 mg, 0.36 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol) and triethylamine (73 mg, 0.72 mmol). The resulting solution was stirred at room temperature for 30 minutes. Then 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (40 mg, 0.24 mmol) was added to the solution, and it was stirred at room temperature for 16 hours. Water (20 mL) was added to the mixture. It was extracted with dichloromethane (50 mL). The organic layer was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography dichloromethane/methanol=10:1 to afford N-((2-hydroxy-4-methoxy-6-methylpyridin-3-yl)methyl)-4-phenoxy benzamide (32 mg, 37%) as a white solid.

Workup

  1. stirringwas stirred at room temperature for 16 hours
  2. extractionIt was extracted with dichloromethane (50 mL)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customto provide crude product which
  5. customwas purified by silica gel column chromatography dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-6d2dbdcd17e24186810e8cf384be1795
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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