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Sodium hydride → 2-(4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile

HRID 1483847
ノート
印刷プレビュー

反応式

HRID 1483847 の反応式
CCOP(OCC)([CH2:6][C:7]#[N:8])=O.CN1C(=O)N(C)CCC1.[H-].[Na+].[Cl:23][C:24]1[CH:25]=[C:26]([C:30]2[N:34]3[N:35]=[C:36]([NH:39][CH:40]4[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]4)[CH:37]=[CH:38][C:33]3=[N:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1>C1COCC1.O.CC(=O)OCC>[Cl:23][C:24]1[CH:25]=[C:26]([C:30]2[N:34]3[N:35]=[C:36]([NH:39][CH:40]4[CH2:45][CH2:44][C:43](=[CH:6][C:7]#[N:8])[CH2:42][CH2:41]4)[CH:37]=[CH:38][C:33]3=[N:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 712277284-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone

生成物 1

HCID 712277332-(4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile収率 72.3%

試薬・触媒・溶媒

3
HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a 0° C. solution of diethyl cyanomethyl phosphonate (0.07 mL, 0.4 mmol) in THF (1.5 mL) was added DMPU (0.27 mL, 1 mmol), followed by NaH (15 mL, 0.37 mmol). After stirring for 10 min, a solution of 4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone (130 mg, 0.38 mmol) in THF (1.5 mL) was added. The resulting mixture was stirred at room temperature for 2 h. TLC (EA) showed most of s.m. was converted into product. The mixture was poured into water (100 mL) and extracted with EtOAc (50 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-(4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile (100 mg, 69%) as a yellow solid.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 2 h
  2. extractionextracted with EtOAc (50 mL*3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-52b5c18ed2e9480c904f7677d65ae668
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09416132B2

反応ノート

読み込み中…

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