Triethylamine → HCID 178425180, compound

HRID 1501154Notes

Reaction equation

HRID 1501154 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH3:9])=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[NH2:48][CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>ClCCl>[OH:58][C:51]1[C:50]([CH2:49][NH:48][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([CH:8]([O:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH3:9])=[CH:18][CH:17]=2)=[C:55]([CH3:56])[CH:54]=[C:53]([CH3:57])[N:52]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89580975HCID 89580975, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425180HCID 178425180, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1-(pyridin-4-yloxy)ethyl)benzoic acid (127 mg, 0.5 mmol), N-hydroxybenzotriazole (101.25 mg, 0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg, 0.75 mmol) and triethylamine (151 mg, 1.5 mmol) in dichloromethane (50 mL) was stirred for 30 minutes at room temperature. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.5 mmol) was added. The resultant mixture was stirred at room temperature for 12 hours. The mixture was washed with water (10 mL×3). The organic layer was concentrated to give a residue and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(pyridin-4-yloxy)ethyl)benzamide (57 mg, 30%). LRMS (M+H+) m/z: calcd 377.17. found 377. HPLC purity (214 nm): 99%. 1H NMR (300 MHz, CD3OD): δ 8.23 (d, J=5.1 Hz, 2H), 7.78 (d, J=8.1 Hz, 2H), 7.46 (d, J=8.1 Hz, 2H), 6.93-6.91 (m, 2H), 6.08 (s, 1H), 5.62 (q, J=6.3 Hz, 1H), 4.47 (s, 2H), 2.34 (s, 3H), 2.23 (s, 3H), 1.64 (d, J=6.3 Hz, 3H).

Workup

  1. washThe mixture was washed with water (10 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customto give a residue
  4. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-f9d756e9109b459f929a5df0e7f25c54
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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