Triethylamine → HCID 178425209, compound

HRID 1500973Notes

Reaction equation

HRID 1500973 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)#[N:2].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:36][CH2:37][C:38]1[C:39]([OH:46])=[N:40][C:41]([CH3:45])=[CH:42][C:43]=1[CH3:44]>O.ClCCl>[C:1]([C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:36][CH2:37][C:38]2[C:39]([OH:46])=[N:40][C:41]([CH3:45])=[CH:42][C:43]=2[CH3:44])=[O:12])=[CH:13][CH:14]=1)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 28604971HCID 28604971, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425209HCID 178425209, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(2-cyanophenoxy)benzoic acid (500 mg, 2.09 mmol), 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride (453 mg, 2.37 mmol), N-hydroxybenzotriazole (320 mg, 2.37 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) was stirred at 25° C. for half an hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (318 mg, 2.09 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 mL) was added 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 vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 4-(2-cyanophenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (400 mg, 51%). LRMS (M+H+) m/z: calcd 373.14. found 373. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.38 (s, 1H), 7.94-7.91 (m, 3H), 7.69 (t, J=8.1 Hz, 1H), 7.37-7.31 (m, 1H), 7.16-7.06 (m, 3H), 5.86 (s, 1H), 4.29 (d, J=4.2 Hz, 2H), 2.17 (s, 3H), 2.11 (s, 3H).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  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 vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-5094750c461b424399eb464e01741f64
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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