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Dimethylformamide → 6-cyano-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide

HRID 1664041
ノート
印刷プレビュー

反応式

HRID 1664041 の反応式
Cl[C:2]1[CH:40]=[CH:39][C:5]([C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:37])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]6([C:35]#[N:36])[CH2:34][CH2:33]6)[CH:27]=5)[CH:19]=4)=[N:13][N:12]3[CH:38]=2)=[O:7])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH3:46][N:47](C)C=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N>[C:46]([C:2]1[CH:40]=[CH:39][C:5]([C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:37])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]6([C:35]#[N:36])[CH2:34][CH2:33]6)[CH:27]=5)[CH:19]=4)=[N:13][N:12]3[CH:38]=2)=[O:7])=[CH:4][N:3]=1)#[N:47]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 575057506-chloro-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide

生成物 1

HCID 575057656-cyano-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide収率 47%

試薬・触媒・溶媒 2

HCID 11186
Zinc cyanide (Zn(CN)2)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

A mixture of 6-chloro-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide (120 mg, 0.201 mmol), tetrakis(triphenylphosphine)palladium (0) (58 mg, 50.4 mol), zinc cyanide (26 mg, 0.225 mmol) and N,N-dimethylformamide (2.5 mL) was stirred with heating under an argon atmosphere at 100° C. for 6.5 hr. After the reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogencarbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (51 mg, 47%) as a yellow powder.

後処理

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

出典と根拠

ORDレコード
ord-3dbb07f7def143a4968bcf0b4eb6c321
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08034812B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート