1,1'-Carbonyldiimidazole → 3-[(Z)-N-[(6-amino-2-pyridinyl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

HRID 2206858Notes

Reaction equation

HRID 2206858 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:12](=[N:14]\[OH:15])\[NH2:13])[CH:5]=[CH:4][CH:3]=1.C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:12]2[NH:13][C:27](=[O:28])[O:15][N:14]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 136626362(2Z)-2-[(6-amino-2-pyridinyl)methoxyimino]-N'-hydroxy-2-phenylethanimidamide

Product 1

HCID 1366263643-[(Z)-N-[(6-amino-2-pyridinyl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-oneYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1Z,2Z)-2-{[(6-aminopyridin-2-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (3 g, 10.51 mmol, 1 eq.) in DMF (50 ml) was added CDI (1.70 g, 10.51 mmol, 1 eq.) and stirring at room temperature was allowed for 30 min before heated to 80° C. for 6 h. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was triturated in MeCN and a white solid was isolated by filtration giving a first crop of 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (1.36 g, 36% yield). The mother liquor was concentrated and purified by chromatography on silica gel to give a second crop (2.9 g, 50% purity, 40% yield).

Workup

  1. temperaturebefore heated to 80° C. for 6 h
  2. customThe reaction was quenched by addition of water
  3. extractionextracted with EtOAc (3×50 ml)
  4. washwashed with aq. sat. NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was triturated in MeCN
  8. customa white solid was isolated by filtration

Sources & evidence

ORD record
ord-f14b8c2c06c04918b29e9be545b588be
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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