Pyrrolidine → HCID 46784126, compound

HRID 1755219Notes

Reaction equation

HRID 1755219 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)C>O1CCOCC1>[N:12]1([C:2]2[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 521913N,N-Diethyl-2-propanamineHCID 13106141Ethyl 2-chlorothiazole-4-carboxylate

Product 1

HCID 46784126HCID 46784126, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-chlorothiazole-4-carboxylate (500 mg, 2.6 mmol), pyrrolidine (210 mg, 2.98 mmol) and diethylisopropyl amine (1 mL) in p-dioxane (5 mL) was heated to 60° C. for 2 h. After cooling to room temperature, the solvent was concentrated in vacuo and the residue purified by flash chromatography (SiO2, 2 to 5% MeOH in CH2Cl2 as eluent) to give the desired compound as a foam (400 mg, 68% yield, which was used directly for the next step). MS: (ES) m/z 227.1 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated in vacuo
  3. customthe residue purified by flash chromatography (SiO2, 2 to 5% MeOH in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-880218f039a4454d872c50402bff0482
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

Loading…