Dimethylformamide → 6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid isopropylamide

HRID 548877Notes

Reaction equation

HRID 548877 reaction equation
I[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN([CH:48]=[O:49])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:22]([NH:25][C:48]([C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1)=[O:49])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 11776TriphenylphosphineHCID 86630896(6-Iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine

Product 1

HCID 671580036-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid isopropylamideYield 20%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of (6-iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine (300 mg, 0.76 mmol) in DMF (3 mL) was added isopropylamine (0.66 ml, 7.6 mmol), triphenylphosphine (20 mg, 0.08 mmol) and palladium(II) acetate (17 mg, 0.08 mmol). The resulting mixture was stirred at room temperature for 16 h under a carbon monoxide atmosphere. After evaporation of the solvent the residue was extracted (ethyl acetate/water). The organic phase was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80) to afford the title compound (55 mg, 20%) as a light yellow oil. MS: m/e=352.3 [M+H]+.

Workup

  1. customAfter evaporation of the solvent the residue
  2. extractionwas extracted (ethyl acetate/water)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80)

Sources & evidence

ORD record
ord-3f07ee7f6ddf430eb35ae002a6a06866
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

Loading…