Triethylamine → HCID 178425194, compound

HRID 1500976Notes

Reaction equation

HRID 1500976 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.C(N=C=NCCCN(C)C)C.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:48][CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:48][CH2:49][C:50]2[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=2[CH3:56])=[O:13])=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22684060HCID 22684060, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425194HCID 178425194, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((3-bromophenoxy)methyl)benzoic acid (0.1 g, 0.32 mmol) in dichloromethane (20 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (147 mg, 0.76 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (104 mg, 0.77 mmol) and triethylamine (77 mg, 0.7 mmol). The mixture was stirred for 0.5 hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (60 mg, 0.4 mmol) was added and the resultant mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with water (20 mL). The organic phase was separated and concentrated to give a residue. The residue was purified through column chromatography (silica gel, dichloromethane/methanol=20:1) to afford 4-((3-bromophenoxy)methyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (80 mg, 57%). LRMS (M+H+) m/z: calcd 440.07. found 440.

Workup

  1. washThe reaction mixture was washed with water (20 mL)
  2. customThe organic phase was separated
  3. concentrationconcentrated
  4. customto give a residue
  5. customThe residue was purified through column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-2ed8c162a7d94dd9b3e96637c2d0aa43
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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