Potassium Iodide → HCID 178465692, compound

HRID 2206861Notes

Reaction equation

[OH:1][N:2]=[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13]/[N:14]=[C:15](\[C:22]2[N:26]([CH3:27])[C:25](=[O:28])[O:24][N:23]=2)/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1)[CH3:4].I[CH2:30][CH:31]1[CH2:33][CH2:32]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C.O>[CH:31]1([CH2:30][O:1][N:2]=[C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13]/[N:14]=[C:15](\[C:22]3[N:26]([CH3:27])[C:25](=[O:28])[O:24][N:23]=3)/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:7]=2)[CH3:4])[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N′-hydroxy-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide (150 mg, 0.392 mmol, 1 eq), iodomethylcyclopropane (0.069 ml, 0.588 mmol, 1.5 eq) and cesium carbonate (191 mg, 0.588 mmol, 1.5 eq) in DMF (3 ml) was stirred at 80° C. for 7 h and overnight at room temperature. Iodomethylcyclopropane (0.069 ml, 0.588 mmol, 1.5 eq), cesium carbonate (191 mg, 0.588 mmol, 1.5 eq) and potassium iodide (0.1 eq) were then added and the mixture was stirred at 60° C. for 8 h. Water was added and the mixture was extracted with ethyl acetate. The organics were combined, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to afford N′-(cyclopropylmethoxy)-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide (20 mg, 10% yield) as a transparent oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialdried over MgSO4
customevaporated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-e91eb2bf19414ab3b845cd8e889ffd3d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375010B2

Reaction notes

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