1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178425176, compound

HRID 1501214Notes

Reaction equation

HRID 1501214 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([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:5][CH:4]=1)#[N:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:42][CH2:43][C:44]1[C:45]([OH:52])=[N:46][C:47]([CH3:51])=[CH:48][C:49]=1[CH3:50]>ClCCl.O.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:8]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:42][CH2:43][C:44]3[C:45]([OH:52])=[N:46][C:47]([CH3:51])=[CH:48][C:49]=3[CH3:50])=[O:16])=[CH:17][CH:18]=2)[CH3:9])=[CH:19][CH:20]=1)#[N:2]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 89580720HCID 89580720, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425176HCID 178425176, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(1-(4-cyanophenoxy)ethyl)benzoic acid (260 mg, 1 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (382 mg, 2 mmol), 1-Hydroxybenzotriazole (270 mg, 2 mmol), triethylamine (0.4 mL) in dichloromethane (55 mL) were stirred at 25° C. for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1 mmol) was added to the above mixture. 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 (50 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was evaporated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 4-(1-(4-cyanophenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (150 mg, 48%) as a white solid. LRMS (M+H+) m/z: cald. 401.17. found 401.

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. extractionthe mixture was extracted with dichloromethane (50 mL×3)
  3. dry with materialThe combined organic phase was dried by sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-7458955d80a94aadaf391472e6a5b55d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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