1,2-Dichloroethane → 3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone

HRID 1172937Notes

Reaction equation

HRID 1172937 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3]1.C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O.[Cl:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[O:36][CH:37]([CH3:39])[CH3:38])/[C:29](=[N:31]/O)/[NH2:30]>CN(C=O)C>[Cl:25][C:26]1[CH:27]=[C:28]([C:29]2[N:31]=[C:7]([CH:4]3[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]3)[O:9][N:30]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH:37]([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 2277983-Oxocyclopentanecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 595565653-chloro-N'-hydroxy-4-propan-2-yloxybenzenecarboximidamide

Product 1

HCID 595565403-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanoneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
140 °C

Procedure

To a slurry of 3-oxocyclopentanecarboxylic acid (0.123 g, 0.962 mmol) in DMF (1.0 ml) was added EDC (0.184 g, 0.962 mmol) followed by HOBT hydrate (0.130 g, 0.962 mmol). After about 1 h a solution of (Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.2 g, 0.875 mmol) in DMF (0.5 ml) was added and the reaction mixture was heated to about 140° C. for about 45 min. After cooling to room temperature the reaction mixture was concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide 3-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)cyclopentanone (0.156 g, 56%) as a yellow oil. LCMS (Table 1, Method c) Rt=2.75 min, m/z 321 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by chromatography on silica gel (eluting with EtOAc/Hep)

Sources & evidence

ORD record
ord-d54c32463ac64a8b81d4433e4c81b040
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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