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

HRID 548877ノート

反応式

HRID 548877 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-3f07ee7f6ddf430eb35ae002a6a06866
出典データセット
uspto-grants-2011_05
特許番号
US07943619B2

反応ノート

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