1-Hydroxybenzotriazole → HCID 178425178, compound

HRID 1501245Notes

Reaction equation

HRID 1501245 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH3:6].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:43][CH2:44][C:45]1[C:46]([OH:53])=[N:47][C:48]([CH3:52])=[CH:49][C:50]=1[CH3:51]>ClCCl.O.C(N(CC)CC)C>[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:43][CH2:44][C:45]2[C:46]([OH:53])=[N:47][C:48]([CH3:52])=[CH:49][C:50]=2[CH3:51])=[O:13])=[CH:14][CH:15]=1)[CH3:6]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581052HCID 89581052, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425178HCID 178425178, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(1-(2,4-difluorophenoxy)ethyl)benzoic acid (127 mg, 0.5 mmol) in dichloromethane (80 mL) was added N-hydroxybenzotriazole (101.25 mg, 0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg, 0.75 mmol) and triethylamine (151 mg, 1.5 mm ol). then the 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.5 mmol) was added, the solution was stirred at room temperature for 12 hours, water was added and washed 3 times, the organic layer was evaporated and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 4-(1-(2,4-difluorophenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (78 mg, 38%).

Workup

  1. washwashed 3 times
  2. customthe organic layer was evaporated
  3. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-bac2aae0a9e441dca11a796a4841c166
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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