Triethylamine → HCID 178425155, compound

HRID 1479740Notes

Reaction equation

HRID 1479740 reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH3:4].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:44][CH2:45][C:46]1[C:47]([OH:54])=[N:48][C:49]([CH3:53])=[CH:50][C:51]=1[CH3:52]>ClCCl>[OH:54][C:47]1[C:46]([CH2:45][NH:44][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([CH:3]([CH:2]([CH3:1])[CH3:14])[CH3:4])=[CH:13][CH:12]=2)=[C:51]([CH3:52])[CH:50]=[C:49]([CH3:53])[N:48]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45117212HCID 45117212, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425155HCID 178425155, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-methylbutan-2-yl)benzoic acid (0.10 g, 0.50 mmol), 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.14 g, 0.7 mmol) and 1-hydroxybenzotriazole (0.10 g, 0.70 mmol) in dichloromethane (20 mL) was added triethylamine (0.2 g, 2.0 mmol). The reaction mixture was stirred at room temperature for 15 minutes, and followed by 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.08 g, 0.5 mmol). The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water, dried by anhydrous sodium sulfate, then the solvent removed in vacuo to give the crude product, which was purified by Prep-TLC (dichloromethane:methanol=20:1) to give the pure product N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(3-methylbutan-2-yl)benzamide (0.08 g, 44%) as a white solid. LR MS (M+H+): calcd for 326.2. found 326. HPLC Purity (214 nm) 99.6%. 1H NMR (CH3OH-d4, 300 MHz): δ 7.71 (d, J=8.1 Hz, 2H), 7.23 (d, J=8.4 Hz, 2H), 6.10 (s, 1H), 4.49 (s, 2H), 2.49-2.44 (m, 1H), 2.37 (s, 3H), 2.24 (s, 3H), 1.82-1.75 (m, 1H), 3.14-3.06 (m, 1H), 1.24 (d, J=7.2 Hz, 3H), 0.96 (d, J=6.6 Hz, 3H), 0.76 (d, J=7.2 Hz, 3H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. washthe mixture was washed with water
  4. dry with materialdried by anhydrous sodium sulfate
  5. customthe solvent removed in vacuo
  6. customto give the crude product, which
  7. customwas purified by Prep-TLC (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-d68808715db4495fba1fcbaeffac4594
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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