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Dimethylformamide → 3-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbonitrile

HRID 68968
ノート
印刷プレビュー

反応式

HRID 68968 の反応式
Cl[C:2]1[C:7]([CH2:8][N:9]([CH2:23][C:24]2[CH:41]=[CH:40][C:27]3[N:28]([CH2:38][CH3:39])[C:29](=[O:37])[C:30]([CH3:36])([CH3:35])[C:31](=[O:34])[N:32]([CH3:33])[C:26]=3[CH:25]=2)[CH2:10][CH2:11][N:12]2[CH:17]=[CH:16][C:15]3[O:18][C:19]([CH3:21])=[CH:20][C:14]=3[C:13]2=[O:22])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:42][N:43](C=O)C>[C-]#N.[Zn+2].[C-]#N.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].O>[CH2:38]([N:28]1[C:29](=[O:37])[C:30]([CH3:36])([CH3:35])[C:31](=[O:34])[N:32]([CH3:33])[C:26]2[CH:25]=[C:24]([CH2:23][N:9]([CH2:8][C:7]3[C:2]([C:42]#[N:43])=[N:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11][N:12]3[CH:17]=[CH:16][C:15]4[O:18][C:19]([CH3:21])=[CH:20][C:14]=4[C:13]3=[O:22])[CH:41]=[CH:40][C:27]1=2)[CH3:39]
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

8

反応物 2

HCID 6228DimethylformamideHCID 866704802-Chloro-3-({(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-[2-(2-methyl-4-oxo-4-H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine

生成物 1

HCID 706571733-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbonitrile

試薬・触媒・溶媒 5

HCID 11186
Zinc cyanide (Zn(CN)2)
触媒
HCID 23994Zinc触媒
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

2-Chloro-3-({(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-[2-(2-methyl-4-oxo-4-H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine (0.3 g), zinc cyanide (120 mg), tris(dibenzylideneacetone)dipalladium (24 mg), 1,1′-bis(diphenylphosphino)ferrocene (14 mg), and zinc powder (3.4 mg) were added to DMF (3 ml), and the mixture was heated at 95° C. for 3 hours. The reaction liquid was cooled to room temperature. Water was added to the reaction mixture and subjected to celite filtration. Extraction with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=93:7). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether to give the title compound (1.35 g) as a white powder.

後処理

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. filtrationsubjected to celite filtration
  4. extractionExtraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=93:7)
  8. customcondensed under reduced pressure
  9. customthe residue was recrystallized from ether

出典と根拠

ORDレコード
ord-4dd881faa6a244ee90c0860607a2b6f7
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822453B2

反応ノート

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