Triethylamine → HCID 178425185, compound

HRID 1501258Notes

Reaction equation

HRID 1501258 reaction equation
[OH:1][CH2:2][CH:3]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:49][CH2:50][C:51]1[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57]>ClCCl>[OH:1][CH2:2][CH:3]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([NH:49][CH2:50][C:51]2[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=2[CH3:57])=[O:17])=[CH:18][CH:19]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581184HCID 89581184, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425185HCID 178425185, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(2-hydroxy-1-phenoxyethyl)benzoic acid (100 mg, 0.3870 mmol), was dissolved into dichloromethane (20 mL), and then N-hydroxybenzotriazole (0.5814 mmol, 80 mg), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.5814 mmol, 112 mg), triethylamine (1.69 mmol, 2 mL) was added to the mixture. After the mixture was stirred at room temperature for 10 minutes, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.387 mol, 58 mg) was added. The mixture was stirred at room temperature for 18 hours. Then washed with water (20 mL), extracted with dichloromethane (20 mL). The organic layer were concentrated and subjected to column chromatography (silica gel, dichloromethane/menthol=15:1) to give 4-(2-hydroxy-1-phenoxyethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (30 mg, 15%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. washThen washed with water (20 mL)
  3. extractionextracted with dichloromethane (20 mL)
  4. concentrationThe organic layer were concentrated

Sources & evidence

ORD record
ord-18fc6b1ab5c9467bbf2864bc6e4e5dcd
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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