Reaction #67728

Reaction equation

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid

Thionyl chloride

N,N-dimethylformamide

pyridin-2-amine

→

product

Yield 10.5%

1-(benzo[d][1,3]dioxol-5-yl)-N-(pyridin-2-yl)cyclopropanecarboxamide

Yield 10.5%

Solvents

pyridine

Conditions

Workup

1. 1
   OtherThe excess thionyl chloride was removed under vacuum
2. 2
   workup.STIRRINGto stir for 15 hours at 110° C
3. 3
   FiltrationThe crude product was then filtered
4. 4
   Otherevaporated to dryness
5. 5
   workup.DISSOLUTIONdissolved in N,N-dimethylformamide (1 mL)
6. 6
   Otherpurified by reverse-phase preparative liquid chromatography

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (41 mg, 0.20 mmol) was placed in an oven-dried flask under nitrogen. Thionyl chloride (0.3 mL) and N,N-dimethylformamide (0.03 mL) were added and the solution was allowed to stir for 10 minutes at room temperature. The excess thionyl chloride was removed under vacuum and the resulting solid was suspended in anhydrous pyridine (1 mL). This solution was then slowly added to a solution of pyridin-2-amine (19 mg, 0.20 mmol) in anhydrous pyridine (1 mL). The resulting mixture was allowed to stir for 15 hours at 110° C. The crude product was then filtered, evaporated to dryness, dissolved in N,N-dimethylformamide (1 mL) and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield the pure product (5.9 mg, 0.021 mmol, 10%). ESI-MS m/z calc. 282.1. found 283.1 (M+1)+. Retention time 2.13 minutes.

Source