Triethylamine → HCID 178425206, compound

HRID 1500954Notes

Reaction equation

HRID 1500954 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][CH2:47][C:48]1[C:49]([OH:56])=[N:50][C:51]([CH3:55])=[CH:52][C:53]=1[CH3:54]>ClCCl>[OH:56][C:49]1[C:48]([CH2:47][NH:46][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:53]([CH3:54])[CH:52]=[C:51]([CH3:55])[N:50]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178425242HCID 178425242, compound

Product 1

HCID 178425206HCID 178425206, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Phenoxybenzoic acid (214 mg, 1.0 mmol), 1-hydroxybenzotriazole (203 mg, 1.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (290 mg, 1.5 mmol) and triethylamine (0.7 mL, 5 mmol) were dissolved in dichloromethane (15 mL). The mixture was stirred at room temperature for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (190 mg, 1.0 mmol) was added to the solution. The mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was concentrated and the residue was purified by column chromatography (silica gel, dichloromethane/methane=40:1) to give the product as a white solid (120 mg, 34%). LRMS (M+H+) m/z: calcd 348.15. found 348. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.28 (m, 1H), 7.86 (s, 1H), 7.83 (s, 1H), 7.40 (t, J=7.2 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.06 (s, 1H), 7.03 (s, 1H), 6.98 (s, 1H), 6.95 (s, 1H), 5.84 (s, 1H), 4.27 (d, J=7.5 Hz, J=3.6, 2H), 2.15 (s, 3H), 2.09 (s, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by column chromatography (silica gel, dichloromethane/methane=40:1)

Sources & evidence

ORD record
ord-f41bc29bdea34f2f9d62050a45536886
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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