2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-(1-{[(1R)-4,9-Dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide

HRID 1943205ノート

反応式

HRID 1943205 の反応式
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C@@H:14]([CH2:15][N:16]4[CH2:21][CH2:20][C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH3:22])[CH2:18][CH2:17]4)[N:3]1[C:4]=23.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[O:12]=[C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][C:2](=[O:1])[N:3]3[C@H:14]([CH2:15][N:16]4[CH2:17][CH2:18][C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH3:22])[CH2:20][CH2:21]4)[CH2:13][N:5]1[C:4]=23

参加物

5

反応物 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11430Potassium CarbonateHCID 86642104N-(1-{[(2R)-4,9-Dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-2-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86642105N-(1-{[(1R)-4,9-Dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide収率 46%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of N-(1-{[(2R)-4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-2-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide (375 mg, 0.909 mmol) in 1,4-dioxane (20 ml) at rt was treated with DDQ (248 mg, 1.091 mmol) and then heated at 80° C. for 1 h. The reaction was then cooled to rt. The reaction mixture was treated with saturated aqueous K2CO3 (5%, 100 ml), then with DCM (100 ml) and the mixture filtered through Kieselguhr. The organic fraction was separated and the aqueous layer extracted with DCM (2×100 ml). The combined organic solvents were then dried (MgSO4), filtered and evaporated to give the crude product as a yellow oil. Chromatography on silica (0-10% methanol:DCM, Rf=0.4 in 10% MeOH/DCM) gave the product as a clear oil (171 mg, 46%).

後処理

  1. temperatureThe reaction was then cooled to rt
  2. filtrationwith DCM (100 ml) and the mixture filtered through Kieselguhr
  3. customThe organic fraction was separated
  4. extractionthe aqueous layer extracted with DCM (2×100 ml)
  5. dry with materialThe combined organic solvents were then dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product as a yellow oil

出典と根拠

ORDレコード
ord-f92e8ae37a564a30bc5d2df720aa50c8
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

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