1,1'-Carbonyldiimidazole → 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-3H-[1,3,4]oxadiazol-2-one

HRID 658362Notes

Reaction equation

HRID 658362 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13].N1([C:25](N2C=CN=C2)=[O:26])C=CN=C1>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]1[O:13][C:25](=[O:26])[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 115888023-[(2-Fluoro-4-iodophenyl)amino]isonicotinohydrazide

Product 1

HCID 248902505-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-3H-[1,3,4]oxadiazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (152 mg, 0.41 mmol) in THF (6 mL) contained TEA (60 μl, 0.43 mmol) were added Di-imidazol-1-yl-methanone (95 mg, 0.57 mmol) at 0° C. The reaction mixture was warmed to RT and stirred for 5 h, additional TEA (40 μl) and CDI (50 mg) were added, and the reaction mixture was stirred overnight at RT. The precipitate was filtered, the solid washed with MeOH. Yield: yellow solid 123 mg. LC-MS (Method A) [5.50 min; 399(M+1)].

Workup

  1. stirringthe reaction mixture was stirred overnight at RT
  2. filtrationThe precipitate was filtered
  3. washthe solid washed with MeOH
  4. customLC-MS (Method A) [5.50 min; 399(M+1)]

Sources & evidence

ORD record
ord-819e41717ed74ccf8fc0cbef0c47c430
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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