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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
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HRID 704636 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 54465980Ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418390
HCID 178418390, 화합물
촉매
HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0c42e2c52dbd4abc8b3b4f979b59904e
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04988698

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