1-Pyrrolidinecarbonyl chloride → HCID 59570315, compound

HRID 1880681Notes

Reaction equation

HRID 1880681 reaction equation
N12CCCN=C1CCCCC2.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[NH:21][O:22][C:23](=[O:25])[N:24]=2)[CH:15]=1.[N:28]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1>N1C=CC=CC=1>[N:28]1([C:33]([N:24]2[C:23](=[O:25])[O:22][N:21]=[C:20]2[C:16]2[CH:15]=[C:14]([C:13]([F:12])([F:26])[F:27])[CH:19]=[CH:18][N:17]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 709371-Pyrrolidinecarbonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178517507HCID 178517507, compound

Product 1

HCID 59570315HCID 59570315, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1 ml of pyridine were added 0.3 g of 1,8-diazabicyclo[5,4,0]undec-7-ene, and 0.3 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one, and 0.26 g of 1-pyrrolidinecarbonyl chloride was added at room temperature. After stirring for 15 hours, the resultant solution was concentrated, and the residue was subjected to silica gel column chromatography to obtain 0.27 g of 4-(1-pyrrolidinecarbonyl)-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (15)).

Workup

  1. additionwas added at room temperature
  2. concentrationthe resultant solution was concentrated

Sources & evidence

ORD record
ord-4240a185bf3f4d7ab13647fdc03f4353
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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