Triethylamine → HCID 178425150, compound

HRID 1501027Notes

Reaction equation

HRID 1501027 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:25][CH2:26][C:27]1[C:28]([OH:35])=[N:29][C:30]([CH3:34])=[CH:31][C:32]=1[CH3:33]>ClCCl>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:25][CH2:26][C:27]2[C:28]([OH:35])=[N:29][C:30]([CH3:34])=[CH:31][C:32]=2[CH3:33])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691474-Benzoylbenzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425150HCID 178425150, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-benzoylbenzoic acid (106 mg, 0.5 mmol), o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethylluroniumhexafluorophosphate (285 mg, 0.75 mmol), triethylamine (152 mg, 1.5 mmol) and dichloromethane (15 mL) were stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.5 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The resultant mixture was washed with water (20 mL). The organic phase was separated, dried over sodium, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give 4-benzyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (50 mg, 29%). LRMS (M+H+) m/z: 346.17. found 346. HPLC purity (214 nm): 97%. 1H NMR (300 MHz, d6-DMSO): δ 11.50 (s, 1H), 8.29 (t, J=4.8 Hz, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.28-7.13 (m, 7H), 5.85 (s, 1H), 4.30 (d, J=4.8 Hz, 2H), 3.96 (s, 2H), 2.16 (s, 3H), 2.11 (s, 3H).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. washThe resultant mixture was washed with water (20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-d472c83334794bc2b47153b0eaae5fb0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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