1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67367073, compound

HRID 1880684Notes

Reaction equation

HRID 1880684 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.[CH:28]([N:31]([CH:35]([CH3:37])[CH3:36])[C:32](Cl)=[O:33])([CH3:30])[CH3:29]>N1C=CC=CC=1>[F:27][C:13]([F:12])([F:26])[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[N:24]([C:32]([N:31]([CH:35]([CH3:37])[CH3:36])[CH:28]([CH3:30])[CH3:29])=[O:33])[C:23](=[O:25])[O:22][N:21]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 87890Diisopropylcarbamoyl chlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 67367073HCID 67367073, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1 ml of pyridine were added 0.28 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 0.3 g of N,N-diisopropylcarbamoyl chloride was added at room temperature. After stirring for 8 hours, the resultant solution was concentrated, and the residue was subjected to silica gel column chromatography to obtain 0.09 g of 3-(4-trifluoromethylpyridin-2-yl)-N,N-diisopropyl-1,2,4-oxadiazol-5-one-4-carboxamide (present compound (18)).

Workup

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

Sources & evidence

ORD record
ord-1923d867951f4e38b2d5e09ea91660f6
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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