1,1'-Carbonyldiimidazole → HCID 71626079, compound

HRID 520257Notes

Reaction equation

HRID 520257 reaction equation
[CH2:1]([N:3]([OH:34])/[C:4](=[N:32]\[H])/[C:5](=[N:12]\[O:13][CH2:14][C:15]1[N:16]=[C:17]([NH:20]C(=O)OCCC2C=CC=CC=2)[S:18][CH:19]=1)/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36]>C(#N)C>[NH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][O:13]/[N:12]=[C:5](/[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)\[C:4]2[N:3]([CH2:1][CH3:2])[O:34][C:35](=[O:36])[N:32]=2)[N:16]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178506481HCID 178506481, compound

Product 1

HCID 71626079HCID 71626079, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-phenylethyl (4-{[({(1Z,2Z)-2-[ethyl(hydroxy)amino]-2-imino-1-phenylethylidene}amino)oxy]methyl}-1,3-thiazol-2-yl)carbamate (160 mg, 71% purity, 0.24 mmol, 1 eq.) in acetonitrile (3 ml), was added 1,1′-carbonyldiimidazole (555 mg, 0.342 mmol, 1.4 eq.). After stirring at 80° C. for 6 hour, the reaction was quenched by addition of water and extracted with EtOAc. The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-ethyl-1,2,4-oxadiazol-5(2H)-one (70 mg, 55% yield).

Workup

  1. customthe reaction was quenched by addition of water
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aea9ed20245b468d91b8e950bb3d1780
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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