Triethylamine → HCID 178428519, compound

HRID 1501264Notes

Reaction equation

HRID 1501264 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:46][C:47]1[CH:52]=[C:51]([CH3:53])[N:50]=[C:49]([OH:54])[C:48]=1[CH2:55][NH2:56]>ClCCl.O>[NH2:46][C:47]1[CH:52]=[C:51]([CH3:53])[N:50]=[C:49]([OH:54])[C:48]=1[CH2:55][NH:56][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178428522HCID 178428522, compound

Product 1

HCID 178428519HCID 178428519, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenoxybenzoic acid (196 mg, 0.91 mmol) in dichloromethane (15 mL) were added 1-hydroxybenzotriazole (177 mg, 1.3 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (251 mg, 1.3 mmol) and triethylamine (265 mg, 2.6 mmol). The resulting solution was stirred at room temperature for 30 minutes. Then 4-amino-3-(aminomethyl)-6-methylpyridin-2-ol (200 mg, 1.3 mmol) was added to the solution, and it was stirred at room temperature for 16 hours. Water (20 ml) was added to the mixture. It was extracted with dichloromethane (50 ml). The organic layer was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford N-((4-amino-2-hydroxy-6-methylpyridin-3-yl)methyl)-4-phenoxybenzamide (180 mg, 57% yield) as a white solid. LRMS (M+H+) m/z: calcd 350.14. found 350. HPLC Purity (214 nm): 97%. 1H NMR (300 MHz, CDCl3): δ 10.71 (d, J=2.4 Hz, 1H), 7.76-7.79 (d, J=8.7 Hz, 2H), 7.32-7.38 (m, 2H), 7.12-7.17 (m, 1H), 6.94-7.02 (m, 4H), 5.64-5.65 (br, 1H), 5.51 (s, 1H), 4.47-4.49 (d, J=6.6 Hz, 2H), 3.48 (s, 2H), 2.16 (s, 3H).

Workup

  1. stirringwas stirred at room temperature for 16 hours
  2. extractionIt was extracted with dichloromethane (50 ml)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customto provide crude product which
  5. customwas purified by silica gel column chromatography with dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-32e8b058fbb44bc9ac1851adb02a18e5
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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