Triethylamine → Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide

HRID 389266Notes

Reaction equation

HRID 389266 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][CH2:10][CH3:11])=[CH:6][C:5]([CH3:12])=[CH:4][N:3]=1.[CH:13]1([C:16]([OH:18])=O)[CH2:15][CH2:14]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH2:8][N:9]([CH2:10][CH3:11])[C:16]([CH:13]2[CH2:15][CH2:14]2)=[O:18])=[CH:6][C:5]([CH3:12])=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58579979(2-Chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amine

Product 1

HCID 58579965Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amine (0.126 g, 0.69 mmol), cyclopropanecarboxylic acid (0.08 mL, 1.03 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.197 g, 1.03 mmol), 1-hydroxybenzotriazole hydrate (0.139 g, 1.03 mmol), and triethylamine (0.29 mL, 2.05 mmol) were combined in CH2Cl2 and stirred at room temperature over the weekend. The mixture was concentrated and purified by silica gel chromatography (0-70% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-80c24559a86542a3bfd7ce65a134546a
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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