2-chloro-5,11-dihydro-11-ethyl-8-[trans-2-(4-pyridyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one → 5-Chloro-2-ethyl-9-methyl-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

HRID 724924ノート

反応式

HRID 724924 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17](/[CH:19]=[CH:20]/[C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[PH2]([O-])=O.[Na+]>O1CCOCC1.O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

参加物

6

反応物 2

HCID 107392322-chloro-5,11-dihydro-11-ethyl-8-[trans-2-(4-pyridyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 178527019HCID 178527019、化合物

生成物 1

HCID 4706665-Chloro-2-ethyl-9-methyl-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one収率 75.3%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 2-chloro-5,11-dihydro-11-ethyl-8-[trans-2-(4-pyridyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (2.3 g, 5.9 mmol) and palladium black (0.25 g) in 30 mL of 1,4-dioxane was added a solution of sodium hypophosphite (0.82 g 7.7 mmol) in 15 mL of water. The reaction mixture was heated at 80°-90° C. for 3 hours. The reaction mixture was then filtered through Celite and extracted with ethyl acetate. The product was purified by chromatography over silica gel, eluting with methanol/dichloromethane, and recrystallized from ethyl acetate/hexanes to give 1.75 g of the title compound as colorless crystals, m.p. 158°-159° C.

後処理

  1. temperatureThe reaction mixture was heated at 80°-90° C. for 3 hours
  2. filtrationThe reaction mixture was then filtered through Celite
  3. extractionextracted with ethyl acetate
  4. customThe product was purified by chromatography over silica gel
  5. washeluting with methanol/dichloromethane
  6. customrecrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-e56c7cd9a2964e0ba22cc2560d470441
出典データセット
uspto-grants-1998_01
特許番号
US05705499

反応ノート

読み込み中…