N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → Methyl 1-[2-fluoro-4-(trifluoromethoxy)phenyl]-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

HRID 1895161Notes

Reaction equation

HRID 1895161 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][N:14]=[C:15]([C:20](=[O:24])[CH2:21][O:22][CH3:23])[C:16]([O:18][CH3:19])=[O:17].[CH:25](OC(OC(C)C)N(C)C)(C)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:10])([F:11])[F:12])[CH:5]=[CH:4][C:3]=1[N:13]1[CH:25]=[C:21]([O:22][CH3:23])[C:20](=[O:24])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:14]1

Participants

4

Reactant 2

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 178496283HCID 178496283, compound

Product 1

HCID 59436184Methyl 1-[2-fluoro-4-(trifluoromethoxy)phenyl]-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 2-{[2-fluoro-4-(trifluoromethoxy)phenyl]hydrazono}-4-methoxy-3-oxobutanoate (3.8 g, 11 mmol) and N,N-dimethylformamide diisopropyl acetal (9.5 mL, 54 mmol) in toluene (60 mL) was refluxed for 5 h. The mixture was concentrated under reduced pressure. The residue was diluted with AcOEt, washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (10/90-100/0 AcOEt/hexane) to give the title compound (3.4 g, 86% yield) as pale yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.91 (3H, s), 3.97 (3H, s), 7.17-7.25 (2H, m), 7.68-7.76 (2H, m).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with AcOEt
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel (10/90-100/0 AcOEt/hexane)

Sources & evidence

ORD record
ord-1cb235d78df048cd9d744b630d2b4276
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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