1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178425222, compound

HRID 1500964Notes

Reaction equation

HRID 1500964 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:40][CH2:41][C:42]1[C:43]([OH:50])=[N:44][C:45]([CH3:49])=[CH:46][C:47]=1[CH3:48]>O.ClCCl.C(N(CC)CC)C>[OH:50][C:43]1[C:42]([CH2:41][NH:40][C:8]([C:6]2[CH:5]=[CH:4][N:3]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:2](=[O:1])[CH:7]=2)=[O:10])=[C:47]([CH3:48])[CH:46]=[C:45]([CH3:49])[N:44]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 89585074HCID 89585074, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425222HCID 178425222, compoundYield 29.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid (60 mg, 0.25 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (95 mg, 0.5 mmol), N-hydroxybenzotriazole (67 mg, 0.5 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) were stirred at 25° C. for half an hour before 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.33 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, was added water (10 ml) and the mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuum. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide as a white solid (28 mg, 29%). LRMS (M+H+) m/z: cald. 377.17. found 377. 1H NMR (300 MHz, d6-DMSO): δ 11.47 (s, 1H), 8.55 (t, J=4.5 Hz, 1H), 7.67 (d, J=6.9 Hz, 1H), 7.38-7.27 (m, 5H), 6.79 (s, 1H), 6.54-6.51 (m, 1H), 6.14 (q, J=7.2 Hz, 1H), 5.85 (s, 1H), 4.23 (d, J=4.5 Hz, 2H), 2.12 (d, J=6.6 Hz, 6H), 1.68 (d, J=7.2 Hz, 3H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (10 mL×3)
  3. dry with materialThe combined organic phase was dried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuum
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-ee20df91997d49fca0263971a18fc45e
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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