Triethylamine → N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamide

HRID 1479753Notes

Reaction equation

HRID 1479753 reaction equation
[CH3:1][CH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.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:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([CH:2]([CH2:3][CH2:4][CH3:5])[CH3:1])=[CH:14][CH:13]=2)=[C:51]([CH3:52])[CH:50]=[C:49]([CH3:53])[N:48]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2812844-(Pentan-2-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178425242HCID 178425242, compound

Product 1

HCID 178442161N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamideYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(pentan-2-yl)benzoic acid (120 mg, 0.66 mmol) in dichloromethane (40 mL) was added N-hydroxybenzotriazole (HOBT) (135 mg, 1.0 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (192 mg, 1.0 mmol), triethylamine (135 mg, 1.5 mmol), stirred for 30 minute. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added and the mixture was stirred at room temperature for 18 hours. The mixture was washed with water (30 mL), dried over anhydrous sodium sulfate, concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) and the obtained solution was freeze-dried to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(pentan-2-yl)benzamide (186 mg, 86.4%) as white solid. LRMS (M+H+) m/z: calcd 326.20. found 326. HPLC Purity (214 nm)95%. 1H NMR (300 MHz, CD3OD): δ 7.72-7.69 (d, J=11 Hz, 2H) 7.29-7.26 (d, J=8.4 Hz, 2H), 6.102 (s, 1H), 4.48 (s, 2H), 2.69-2.62 (m, 1H), 3.36 (s, 3H), 2.24 (s, 3H), 1.66-1.57 (m, 2H), 1.22-1.25 (d, J=9 Hz, 3H), 0.782-0.832 (t, J=7.5 Hz, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. washThe mixture was washed with water (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)
  6. customthe obtained solution was freeze-dried

Sources & evidence

ORD record
ord-bbc2f6dd850e4eb5beb9ca7a9d865abc
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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