1-Hydroxybenzotriazole → HCID 178425189, compound

HRID 1501139Notes

Reaction equation

HRID 1501139 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C@H:6]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[CH3:7].Cl.C([N:23]=[C:24]=[N:25][CH2:26][CH2:27][CH2:28]N(C)C)C.ON1C2C=CC=C[C:36]=2N=N1.[NH2:42][CH2:43][C:44]1[C:45]([OH:52])=[N:46][C:47]([CH3:51])=[CH:48][C:49]=1[CH3:50]>ClCCl.C(N(CC)CC)C>[NH2:23][C:24]1[N:25]=[CH:26][C:27]([C:2]2[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=2)[O:5][C@H:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:42][CH2:43][C:44]3[C:45]([OH:52])=[N:46][C:47]([CH3:51])=[CH:48][C:49]=3[CH3:50])=[O:14])=[CH:15][CH:16]=2)[CH3:7])=[CH:28][CH:36]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 118562724HCID 118562724, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425189HCID 178425189, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (S)-4-(1-(3-bromophenoxy)ethyl)benzoic acid (0.5 g, 1.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.36 g, 1.87 mmol) and N-hydroxybenzotriazole (0.25 g, 1.87 mmol) in 20 mL of dichloromethane was added 0.4 g of triethylamine. The reaction mixture was stirred for 15 minutes at room temperature, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.26 g, 1.71 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with Sodium Bicarbonate (aq), concentrated and purified by column chromatography (silica gel, dichloromethane/meth anol=20:1) to give (S)-4-(1-(3-(6-aminopyridin-3-yl)phenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as the white solid (0.61 g, 86%)

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. washthe mixture was washed with Sodium Bicarbonate (aq)
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica gel, dichloromethane/meth anol=20:1)

Sources & evidence

ORD record
ord-eeea5cef74bf461dba360d1b5d4d7bc7
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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