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Dichloromethane → 6-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinone

HRID 704636
ノート
印刷プレビュー

反応式

HRID 704636 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]([CH:28]=[CH:29][C:30](OCC)=[O:31])[C:22]([N+:25]([O-])=O)=[CH:23][CH:24]=4)[CH2:15][CH2:14]3)=[O:12])[N:10]=[C:4]2[CH:3]=1.ClCCl.[H][H]>[C].[Pd].CO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]5[C:22](=[CH:23][CH:24]=4)[NH:25][C:30](=[O:31])[CH2:29][CH2:28]5)[CH2:15][CH2:14]3)=[O:12])[N:10]=[C:4]2[CH:3]=1
参加物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 6344DichloromethaneHCID 54465980Ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 200727986-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinone収率 78.7%

試薬・触媒・溶媒 2

HCID 178418390
HCID 178418390、化合物
触媒
HCID 887Methanol溶媒

実験手順

A mixture of ethyl 3-[3-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylate (926 mg), 10% palladium carbon (139 mg), dichloromethane (50 ml) and methanol (50 ml) was hydrogenated under one atmospheric pressure of hydrogen at ambient temperature for 2.5 hours. After filtration, acetic acid (1 ml) was added to the filtrate containing ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl-1-piperazinyl]-6-aminophenyl]propionate and 6-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone and evaporated in vacuo. The residue was dissolved in chloroform (30 ml) and washed with saturated aqueous solution of sodium hydrogene carbonate. The extract was dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 6-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(lH)-quinolinone (612 mg).

後処理

  1. filtrationAfter filtration, acetic acid (1 ml)
  2. additionwas added to the filtrate
  3. additioncontaining ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl-1-piperazinyl]-6-aminophenyl]propionate and 6-[4-(7-methylimidazo[1,2-a]-pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in chloroform (30 ml)
  6. washwashed with saturated aqueous solution of sodium hydrogene carbonate
  7. dry with materialThe extract was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized from ethanol

出典と根拠

ORDレコード
ord-0c42e2c52dbd4abc8b3b4f979b59904e
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04988698

反応ノート

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