1-Pyrrolidinecarbonyl chloride → HCID 59570376, compound

HRID 1880714Notes

Reaction equation

HRID 1880714 reaction equation
N12CCCN=C1CCCCC2.[F:12][C:13]([F:30])([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:24]2[NH:25][O:26][C:27](=[O:29])[N:28]=2)[CH:19]=1)[C:14]([F:17])([F:16])[F:15].[N:31]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1>N1C=CC=CC=1>[N:31]1([C:36]([N:28]2[C:27](=[O:29])[O:26][N:25]=[C:24]2[C:20]2[CH:19]=[C:18]([C:13]([F:12])([F:30])[C:14]([F:15])([F:17])[F:16])[CH:23]=[CH:22][N:21]=2)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 709371-Pyrrolidinecarbonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178517502HCID 178517502, compound

Product 1

HCID 59570376HCID 59570376, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2 ml of pyridine were added 0.16 g of 1,8-diazabicyclo[5,4,0]undec-7-ene, and 0.2 g of 3-(4-pentafluoroethylpyridin-2-yl)-1,2,4-oxadiazol-5-one, and 0.14 g of 1-pyrrolidinecarbonyl chloride was added at room temperature. After stirring for 4 hours, the resultant solution was concentrated, and the residue was subjected to silica gel column chromatography to obtain 0.17 g of 4-(1-pyrrolidinecarbonyl)-3-(4-pentafluoroethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (63)).

Workup

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

Sources & evidence

ORD record
ord-d3fce6b974324ab99e4f82319b557964
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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