Triethylamine → HCID 89581524, compound

HRID 1501185Notes

Reaction equation

HRID 1501185 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[O:11])[NH:5][C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9].[OH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[CH3:9][C:8]1[CH:7]=[C:6]([CH3:10])[NH:5][C:4](=[O:11])[C:3]=1[CH2:2][NH:1][C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:18]2[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][OH:12])[CH2:20][CH2:19]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 17606053HCID 17606053, compound

Product 1

HCID 89581524HCID 89581524, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (70 mg, 0.46 mmol), 4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)benzoic acid (122 mg, 0.46 mmol), o-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (210 mg, 0.55 mmol) and triethylamine (70 mg, 0.69 mmol) in anhydrous dichloromethane (5 mL) was stirred at room temperature for 15 hours. Then the mixture was filtered and the solid was washed with water (10 mL), methanol (10 mL) and dichloromethane (10 mL) in turns to give N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)benzamide as white solid (30 mg, 16.4%). LRMS (M+H+) m/z: calcd 398.23. found 398. HPLC purity (214 nm): 89%.

Workup

  1. filtrationThen the mixture was filtered
  2. washthe solid was washed with water (10 mL), methanol (10 mL) and dichloromethane (10 mL) in turns

Sources & evidence

ORD record
ord-48b7f4316da24d72a7f759c7617e24e1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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