2,4,6-Trimethylpyridine → HCID 54180408, compound

HRID 718149Notes

Reaction equation

HRID 718149 reaction equation
Cl.[C:2](=[NH:10])([O:7][CH2:8][CH3:9])[C:3]([CH3:6])([CH3:5])[CH3:4].N1C(C)=CC(C)=CC=1C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:10]=[C:2]([O:7][CH2:8][CH3:9])[C:3]([CH3:6])([CH3:5])[CH3:4])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 10928Ethyl chloroformateHCID 12235056Propanimidic acid, 2,2-dimethyl-, ethyl ester, hydrochloride

Product 1

HCID 54180408HCID 54180408, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl pivalimidate hydrochloride (Example B3) (0.75 g, 4.5 mmol) was suspended in hexanes (11.3 mL) and DCM (11.3 mL) and cooled to 0° C. 2,4,6-Collidine (2.1 mL, 15.9 mmol) and ethyl chloroformate (0.98 g, 9.1 mmol) were sequentially added and the reaction mixture was allowed to warm to RT and stirred for 12 h. The solvent was removed in vacuo and the residue was slurried with EtOAc (50 mL). The solids were removed by filtration through a pad of diatomaceous earth. The filter cake was washed with EtOAc (3×10 mL) and the combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonylpivalimidate (0.81 g, 89%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 4.05 (q, J=7.1 Hz, 2H), 3.95 (q, J=7.0 Hz, 2H), 1.18 (t, J=7.1 Hz, 3H), 1.18 (t, 7.1 Hz, 3H), 1.15 (s, 9H).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe solids were removed by filtration through a pad of diatomaceous earth
  3. washThe filter cake was washed with EtOAc (3×10 mL)
  4. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-86f803d953e7490c816f42c0bfdd18e8
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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