Pyridine → N-(4-Bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinamide

HRID 2042809Notes

Reaction equation

HRID 2042809 reaction equation
ClC(N(C)C)=C(C)C.[F:9][CH:10]([F:27])[CH2:11][O:12][C:13]1[N:21]=[C:20]([NH:22][CH3:23])[C:19]([N+:24]([O-:26])=[O:25])=[CH:18][C:14]=1[C:15]([OH:17])=O.N1C=CC=CC=1.[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1>C(Cl)Cl.C1COCC1>[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH:39][C:15](=[O:17])[C:14]2[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[C:20]([NH:22][CH3:23])=[N:21][C:13]=2[O:12][CH2:11][CH:10]([F:9])[F:27])=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 78074-BromoanilineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 866692912-(2,2-Difluoro-ethoxy)-6-methylamino-5-nitro-nicotinic acid

Product 1

HCID 86664893N-(4-Bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1-Chloro-2-methyl-propenyl)-dimethylamine (1.54 mL, 5.63 mmol) is added to 2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinic acid (880 mg, 5.12 mmol) in DCM (15 mL) and THF (15 mL) and stirred at rt for 15 min. Pyridine (607 μL, 7.67 mmol) followed by 4-bromoaniline are added to the reaction mixture and it is stirred for 1 h at rt. The mixture is concentrated, diluted with water and filtered. The filtercake is washed with water and dried to give the sub-title compound.

Workup

  1. additionare added to the reaction mixture and it
  2. stirringis stirred for 1 h at rt
  3. concentrationThe mixture is concentrated
  4. additiondiluted with water
  5. filtrationfiltered
  6. washThe filtercake is washed with water
  7. customdried

Sources & evidence

ORD record
ord-ceb475c2afcb4036adf44ebe80ed0543
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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