Triethylamine → 5,6-dichloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)nicotinamide

HRID 1517315Notes

Reaction equation

S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([OH:13])=O.C(N(CC)CC)C.[CH3:23][NH:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)(Cl)Cl.O.O1CCCC1>[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([N:24]([CH3:23])[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:13]

Participants

Conditions

Temperature: 90 °C

Procedure

Thionyl chloride (6 ml) was added to 5,6-dichloronicotinic acid (600 mg, 3.13 mmol), and stirred under a nitrogen atmosphere at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure, and with cooling with ice, triethylamine (1.31 ml, 9.38 mmol) and N-methyl-2-pyrrolidin-1-ylethanamine (481 mg, 3.75 mmol) were added to a tetrahydrofuran solution (4 ml) of the obtained residue, and stirred at room temperature for 3 minutes. Saturated saline water and chloroform were added to the reaction solution, the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1) to obtain 5,6-dichloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)nicotinamide 967 mg) as an orange oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
stirringstirred at room temperature for 3 minutes
dry with materialthe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record: ord-08749f339c7d43c396e39bb3178fb5c4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232284B2

Reaction notes

Loading…