1,1'-Carbonyldiimidazole → HCID 57636821, compound

HRID 2387363Notes

Reaction equation

HRID 2387363 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[C:22]([C:30]([NH:32][NH2:33])=[O:31])=[CH:23][N:24]([CH3:29])[C:25](=[O:28])[C:26]=2[CH3:27])=[C:16]([F:34])[CH:15]=1>CN(C=O)C.C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[C:22]([C:30]3[O:31][C:1](=[O:2])[NH:33][N:32]=3)=[CH:23][N:24]([CH3:29])[C:25](=[O:28])[C:26]=2[CH3:27])=[C:16]([F:34])[CH:15]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 666742204-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide

Product 1

HCID 57636821HCID 57636821, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-Carbonyldiimidazole (275 mg, 1.70 mmol) was added to a stirred solution of 4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide (728 mg, 1.62 mmol (82% pure material)) in DMF (2 mL). After 1 hour, the reaction mixture was diluted with ethyl acetate and washed with brine. Some of the product precipitated and was collected by filtration. The filtrate was diluted with 1 N HCl and the layers separated. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting residue was triturated with diethyl ether to give the desired product which was combined with the earlier obtained product. The combined yield of clean desired product was 482 mg (75%); MS APCI (−) m/z 393, 395 (M−, Br pattern) detected; 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.88 (s, 1H), 7.50 (dd, 1H), 7.21 (d, 1H), 6.59 (t, 1H), 3.52 (s, 3H), 1.76 (s, 3H).

Workup

  1. washwashed with brine
  2. customSome of the product precipitated
  3. filtrationwas collected by filtration
  4. additionThe filtrate was diluted with 1 N HCl
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-0b4c880b85644f8aad23cf2362e36ed0
Source dataset
uspto-grants-2012_09
Patent number
US08268852B2

Reaction notes

Loading…