Water → N-{5-[(2-{[(ethylamino)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1663910

反応式

HRID 1663910 の反応式
Cl.[NH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:17]=3)=[N:7][N:6]2[CH:29]=1.[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31].C(OCC)(=O)C.O1CCCC1.O>N1C=CC=CC=1>[CH2:30]([NH:32][C:33]([NH:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:17]=3)=[N:7][N:6]2[CH:29]=1)=[O:34])[CH3:31]

参加物

6

反応物 4

HCID 962WaterHCID 8022Ethyl isocyanateHCID 21939870Tetrahydrofuran ethyl acetateHCID 57505635N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride

生成物 1

HCID 57505647N-{5-[(2-{[(ethylamino)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 74.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (200 mg, 0.48 mmol) in pyridine (3 mL) was added ethyl isocyanate (380 μL, 4.8 mmol), and the mixture was stirred at room temperature for 2 hr. Ethyl acetate/tetrahydrofuran and water were added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0) to give the title compound (160 mg, 72%) as a pale-yellow solid.

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0)

出典と根拠

ORDレコード
ord-b812f465cbb349c49e149c704b45c6ec
出典データセット
uspto-grants-2011_10
特許番号
US08034812B2

関連ノート

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